


iron hearts all turn to rust

by Rinniebee



Series: Be That As It May [2]
Category: Gilmore Girls
Genre: Alternate Universe, Best Friends, Drama, Eventual Smut, F/M, Family, Friends to Lovers, Humor, Romance, Sex, Sexual Content, Unresolved Romantic Tension, Unresolved Sexual Tension
Language: English
Status: Completed
Published: 2016-12-31
Updated: 2017-02-01
Packaged: 2018-09-13 18:33:40
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 12
Words: 103,155
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9136471
Author URL: https://archiveofourown.org/users/Rinniebee/pseuds/Rinniebee
Summary: She sighed, twisting onto her back to glance at Jess in the dark. This was all so ridiculous; he was her best friend. She could touch him if she wanted to, he wouldn’t think she was weird or that she was making a sexual advance. They cuddled all the time, her head on his shoulder, his fingers playing with her hair. It was just the bed that made the action seem intimate, but it didn’t have to be.In the end she made the choice not to touch him.





	1. Chapter 1

**Author's Note:**

> Okay!! So here's chapter one to go with 'break this only if...'. If you haven't read that one go read it so that the final scene between Paris and Rory makes sense to you, or you can read it after if you wish. This fic is quite AU, so some things that happened in the show didn't happen or they just straight up happened in another way. 
> 
> Anyway!! Don't forget to give kudos if you liked it and leave a comment, as I love hearing all your thoughts!

**AGE SIXTEEN, SEPTEMBER. STARS HOLLOW**

“Are you sure you can handle a kid like Jess?”

Rory pressed herself up quietly against her door, breathing shallow and careful. Her heart was thumping wildly, but she willed it to be quiet, not wanting to miss a single detail of the conversation happening just outside her door. It wasn’t often that Luke came over to their house to talk. He mostly came in to do handy work for her mother and then leave as quickly as possible; Rory always joked that it was his way of making sure he didn’t look like he cared too much.

“He’s my nephew, Lorelai,” Luke argued, a sort of defiance present in his tone. “I was raised to take care of my family no matter what.”

Rory worried at her bottom lip and fought off the desire to stomp into the kitchen and demand to know what was going on. She’d never considered herself a nosy kid per se, but this had something to do with her—kind of. She’d met Jess at the age of eleven at her birthday party. He had stood out like a sore thumb amongst all the townies in her home, and aside from her and Lane, he was the only other kid there. Her mother had introduced him as Luke’s nephew, and they’d talked a little bit but Jess wasn’t exactly an easy person to get to know in one chance meeting. Over time, they’d run into each other again whenever he was here visiting for an unannounced amount of time and they’d struck up an odd friendship based on a love of books, movies, and music.

“I’m not saying you shouldn’t take care of him, but he’s sixteen and reckless. Do you even have any experience with taking care children on your own at all?! As a mother to a sixteen-year-old, I feel confident in saying that you are not prepared for raising one!”

“Well, I guess it’s a good thing that I don’t need your approval then! Look, Lorelai, his mother is unreliable, he’s gone a full two weeks without a proper meal, he can't take it at home anymore and so he’s coming here to stay! End of story!”

Rory almost jumped out of her skin when she heard the back door slam and her mother started stomping around the kitchen. She rushed back to her bed, grabbed her walkman and slipped on her headphones just before her mother walked in. No music was playing, but she tried to look convincing. Lorelai eyed her from the doorway, her mouth set up into her _I’m really pissed off_ frown.

“I’m guessing you heard all of that?” She asked, and Rory did her best to play it cool.

“What?” Rory asked, pretending to not have heard her. She pulled her headphones down and let them hang around her neck. “Sorry. Music. What happened? You look upset.”

Lorelai sighed, throwing her hands up in the air in her frustration. She wandered over to Rory’s bed and flopped down onto her back, hands covering her face as she groaned, feet flailing wildly. Rory stared at her, waiting for her to sit up, and when it finally happened her mother said, “Jess is coming to Stars Hollow to stay.”

“Like… indefinitely?” Rory asked, already knowing the answer, but she did want confirmation.

“Yep, seems that way.”

“Wow.” She tried to ignore the happy spark trying to start a forest fire in her chest, but she couldn’t wait to tell Lane about this. “Things haven’t gotten any better with his mom?”

Lorelai looked pained as she shook her head. “If anything they’ve gotten worse…”

“Poor Jess,” Rory said and meant it; as happy as she was that he was coming here to stay, the circumstances didn’t seem all that great. Two whole weeks without a proper meal? How could his mother be so cruel? “But Luke will take good care of him, right?”

“Yeah,” Lorelai nodded, looking grim. “It’s just… he’s never raised a kid before. Jess is self-sufficient, like you, but he’s also unpredictable and this could turn out really badly for both of them.”

“You don’t know that,” Rory argued, placing her walkman back on her dresser and removing her headphones from her neck. “This could be the best thing that ever happens to Jess and Luke!”

Lorelai just shrugged before she said, “I hope you’re right, Kid," in a rather defeated voice.

  


**AGE TWENTY-TWO, SEPTEMBER. PHILADELPHIA**

Rory watched as Jess leaned into the back of her trunk to grab the last of the moving boxes. He hoisted the remaining two into his arms, biceps flexing, before making his way to the apartment door. She held it open for him to get down into her new home with ease, silently admiring his walk and how good he looked in dark wash jeans.

Once they were inside, Jess placed the two boxes down on the marble tile and stretched his arms over his head, cracking his back with a slight wince.

“Old man,” Rory cooed at him, patting his cheek as she walked by.

Jess scowled back at her playfully. “You should be grateful that I’m even doing this. This is not a one man job.”

“Yeah, but Luke would kill you if you left me to do it on my own.”

“He’s just lucky I owe him for a lifetime.”

Rory snorted with the quick roll of her eyes. “When are you going to stop thinking that?”

He shrugged back at her. “Probably never,” he answered truthfully.

“Luke took you in because he wanted to. Raising you was not a chore, and it was not favour. It was a fully informed, well-made decision. You don’t _owe_ him for doing something he genuinely wanted to do.”

“Yeah, but it’s not like I was the easiest kid to deal with.”

“You could’ve been a lot worse,” she retorted, hating how self-deprecating he could be sometimes. “You went to school, did your homework, worked two jobs and still managed to graduate at the top of your class. You were a good friend to me, Lane, and Paris—the latter of which, is no small feat—and sure, you and I fought sometimes but you act like you were the devil or something. You were not the devil, Jess.”

“I hate it when you’re nice,” he mumbled himself more than anything but Rory still caught it. “You need my help organizing this stuff?”

She beamed at him, fighting the urge to tease him about his heart of gold. “Help would be nice.”

“Alright. Tell me what goes where.”

They didn’t finish organizing and unpacking her personal items until around one in the morning. They shared an extra large box of pizza and a bottle of wine until they were completely distracted by some horrible R-rated movie on television. Rory made a mental note to thank Mr. Greene for giving her electronics, furniture, wifi and cable practically free of charge. Jess thought it was fishy, but Rory certainly was not about to complain.

“I should probably get going,” Jess said through a yawn, moving to get up from his spot on the couch.

Rory frowned at him, grasping him by the forearm and forcing him back down. “It’s late, I don’t want you driving. Plus, you drank a lot of wine.”

“I think I’m sober now, honestly. The buzz is gone for me.”

She shook her head. “Don’t risk it. I will not be responsible for your death. Luke will be devastated.”

He threw her a pointed look, eyebrows raised. “Just Luke?”

“Are you expecting tears from my mom? ‘Cause you might get tears of joy.”

“Ouch.” He laid his hand on his heart. “I thought she liked me now.”

“She tolerates you.”

Jess shrugged. “Fair enough.”

“I would be devastated as well,” she admitted before tacking on, “Lane and Paris, too.”

“I think Paris might be in Lorelai’s camp. Tears of joy. Finally, the annoying author is dead!”

“No way!” Rory shook her head vehemently. “Paris _loves_ you, Jess. Not as much as me, but still.”

Jess rolled his eyes. “Why is it always a competition with you two?”

“I love you the most, it’s fact!” She said childishly, pushing herself up from the couch. There was still a nice head rush from the wine when she grabbed his hand and started off toward her bedroom. “I was your best friend first, so therefore I get dibs on you.”

“Why do you need dibs?" He asked flirtatiously. "Just what are you planning on doing with me, Gilmore?”

She threw him a saucy look over her shoulder and he stilled, stumbling into her a bit when she continued to yank him forward. Rory let go of his hand once they made it to her room, she grinned with a confidence she only had when drunk and alone with him. He stared at her with wide, blown out eyes.

“Let’s go to bed.”

“I can just sleep on the couch, Rory,” Jess said, now too serious for her liking.

Rory shook her head at him. “That couch doesn't seem comfortable for sleeping. You can sleep here. We’ve shared a bed before, it’s not that big of a deal.” She moved around to the right hand side of the bed and looked at him, head cocked to the side. “Unless you’d prefer the couch?”

Jess opened his mouth to say something, but he quickly closed it after and made his way to the left side, pulling the covers back. “I get hot when I sleep,” he warned her just before removing his shirt, standing in front of her bare chested. She kept her eyes on his face, already knowing what his abs looked like. Jess may have hated the beach, but that didn't mean she didn't still force him to go.

“Yeah, me too,” she said with a shrug, wiggling out of her jeans and crawling into the covers in just tank top and underwear. “We’re adults, Jess. Nothing’s going to happen unless we want it to.” Those words sounded so unlike herself, even to her own ears, and she wondered how it alcohol could make her so bold but it’d been her lucky charm with Logan, too.

“You mind if I take off my pants?”

“Not at all.”

When they’d crawled into bed, they laid on the opposite sides of one another, careful not to touch. Rory could feel the buzz of the wine starting to fade and her doubts were setting in. God, what had she been thinking inviting Jess to share her bed? The couch was fine, more than fine, really. She’d originally thought she could’ve slept there for the rest of her life, but there was always something that happened to her when she got a little drunk. It’d been a couple of months since her final breakup with Logan and she hadn’t gone this long without intimacy since before she’d had sex for the very first time.

The summer, fall and winter months of last year had been her longest dry spell since her freshman year at Yale. She didn’t have time for dating, she’d been on a very serious job hunting grind. The New York Times fellowship had fallen through, and she was too stupid to take the job in Providence, somehow believing it was beneath her. Then, of course, Hugo had offered her an amazing opportunity on Senator Obama’s campaign trail but life had gotten in the way of that, and she’d been so frustrated with just about everything that she’d wanted to cry. In fact, she’d spent a whole week crying, but she’d picked herself back up eventually.

Philadelphia really just happened on a whim. Jess had told her that the Philly branch of the Metro happened to be hiring and he’d put in her resume with a contact he had there—a girl named Val whose father was a board member or something. She hadn’t expected it to go anywhere, in fact, she’d expected to be told she wasn’t good enough since that seemed to be the pattern, but then she got the call for an interview, and then a callback, and then an offer.

She sighed, twisting onto her back to glance at Jess in the dark. This was all so ridiculous; he was her best friend. She could touch him if she wanted to, he wouldn’t think she was weird or that she was making a sexual advance. They cuddled all the time, her head on his shoulder, his fingers playing with her hair. It was just the bed that made the action seem intimate, but it didn’t have to be.

In the end she made the choice not to touch him.

  


**AGE SIXTEEN, DECEMBER. STARS HOLLOW**

“So…” Luke started, rubbing at the back of his neck awkwardly as he tried to start up conversation with his nephew. “You and Liz have any Christmas or Birthday traditions I should know about?”

Jess stared at him, his eyes dull with a hint of disdain at the mention of his mother. “No.”

“Nothing? Not even like a simple birthday cake with candles and singing?”

“Nope,” Jess said, now avoiding eye contact by rummaging through his duffle bag.

He hadn’t brought much with him, just a single beat up duffle stuffed with some clothes but mostly books and music. Liz refused to send down any of his belongings, saying that if he wanted it so bad he could come home and get it himself. Luke had always loved his sister, but in that moment he felt a little bit of hatred for her.

“Would you maybe… want to do something?” Luke asked, stumbling over his words. He was still figuring out the best way to approach Jess; the kid was flighty and stand-offish. He’d learned that if he approached too quickly, Jess would clam up and bolt. He needed to take things slow. It was a process, but he was starting to see results. Just last night, they’d even had a short conversation over dinner.

“Not really,” said Jess, finally looking back up at his uncle; he’d pulled out nothing from his bag.

Luke bobbed his head, figuring that would’ve been the answer. “Okay, that’s fine by me. I’m not really the birthday party type but I think Rory wanted to maybe throw you something, I don’t know.”

“Rory wants to throw me a party? Why?”

“She considers you one of her best friends.”

“She does?” It almost hurt Luke to see his nephew in such disbelief over the truth.

“Yeah,” Luke assured, rocking back and forth on his heels, hands in his pocket. “She does.”

“Huh.”

Luke smiled then, noting the way Jess seemed to be fighting against one of his very own.

  


**AGE TWENTY-THREE, OCTOBER. PHILADELPHIA**

“Why is it snowing?!” Rory demanded to know, flicking her windshield wipers on. “It’s only October! I expect rain and dying trees, not this shit!”

Jess laughed a little beside her, keeping his eyes on his book. “You’re from Connecticut, how are you not used to this by now?”

“Oh, I’m plenty used to it, I just don’t like it.”

“Tough luck, buddy.”

She threw him a small glare that he didn’t see before turning her eyes back to the road. They were almost back at her place now, though she wasn’t entirely happy to be going back. She’d only been living here for about eight months and already she hated it. Philadelphia itself wasn’t the problem, the problem was her landlord, Mr. Greene, and the shitty housing she’d wound up moving into.

The basement apartment really was beautiful for all intents and purposes—white marble floors, a beautiful white kitchen, a bedroom and an office with a full sized bathroom that had a claw-foot bath, _and_  the whole thing came fully furnished. Unfortunately, Jess had been right. Her living situation really was fishy.

The first issue came just a month after living there. Mr. Greene was loud and rowdy; his footsteps were almost like earth quakes and he always had the TV up so loud that Rory could hear every single word of The Big Bang Theory. It was so awful that it often took Rory out of whatever good mood she was in by the got home. In fact, she dreaded going home. She spent most nights at Jess, Matt and Chris’ apartment despite it being further away from work. She just couldn’t deal with Mr Greene using up all the hot water in the mornings, and how he always seemed to be doing laundry when she needed to do a load, making it extremely hard to find a balance.

Even her mother had questioned how she was able to find such a nice apartment for so damn cheap, and now she knew. Mr. Greene couldn’t keep a tenant, so he had to reel in naive people like herself with a good deal. Unfortunately for him, Rory knew her worth, and she had pretty much reached her breaking point by the end of the summer and tonight had brought upon the final straw.

“I still can’t believe the pipes froze and burst!” Rory blurted out angrily; she was gripping the steering wheel so hard that her knuckles had turned white.

She’d gotten the call from Mr. Greene while out having a drink with a beautiful mishmash of her and Jess’ co-workers-slash-friends. Mr. Greene, of course, seemed rather nonchalant about the idea that some of Rory’s personal belongings could’ve been damaged in the flood. She’d almost started crying on the phone, struggling to make sense of what had happened amongst the loud chatter of her friends and the music of the bar. Jess leaned in close, took her cellphone gingerly out of her hand and argued with her landlord on her behalf, one finger pressed into his other ear so he could focus. She could’ve kissed him in that moment.

“I know,” Jess said, voice soothing and calm. He’d finally looked up from his book and he patted her shoulder comfortingly, no longer trying to jibe. “But there’s nothing we can do until we assess the damage. The good thing is, none of that furniture is yours.”

She parked in the driveway of the place she called home and turned off the engine just before turning to face him. “Either way I have no place to live now!” She said on the verge of tears once again and Jess squeezed her shoulder. “I probably have to buy all new electronics and maybe even clothes depending on if they were ruined and how long they've been sitting in the water. Thank god I brought my laptop with me to work this morning.”

“Hey,” Jess said softly, rubbing his thumb up and down her arm. "It's okay, don't cry. You can crash with me for however long you need to. Whatever you lose here, I’ll help you replace.”

Rory sniffed, wiping at her eyes. “I can’t crash with you, Jess… You already have three people in a two bedroom apartment!”

He shrugged. “So? You sleep over all the time anyway.”

“I only sleep over sometimes! Mainly when Mr. Greene is particularly insufferable.”

“Okay, so up _only sometimes_ to _all the time_. It’s not a big deal, Rory. Matt and Chris won’t mind—in fact, I’m sure they’d be thrilled. They like you more than me.”

She hiccuped when she tried to argue against him, and she shivered when she forced a sob down. She would not cry.

“Shh,” Jess whispered as he brushed a piece of hair away from her face. “It’s going to be okay. We can share my room like we always do when you spend the night. I’ll let you have the closet and I’ll even buy you a bookshelf.”

Rory laughed, though it sounded more like cross between a huff and a sob. “I hate it when you’re nice.”

“That’s my line.” He smirked, stroking the top of her head.

“Well, I’m stealing it for today… You’re a good friend, Jess.”

He dipped his head low to his chest so she wouldn’t see his blush, but he wasn’t quite fast enough.

“C’mon,” he said, unclipping his seat belt and opening up the passenger side door, “let’s go break your lease.”

  


**AGE SEVENTEEN, DECEMBER — JESS’ BIRTHDAY. STARS HOLLOW**

Jess really didn’t know what to make of Rory Gilmore. He’d considered her his friend at the age of thirteen when his mother had taken him to Stars Hollow for a visit and wound up leaving him with his Uncle Luke for a month. He spent most of his time with Rory at the diner talking about books, music, and their shitty parents (Christopher for Rory and Jimmy and Liz for Jess). Sometimes Lane joined them and they ventured out into town looking for something to do—not that there was anything to do. Most of the time they got pizza or scouted out Al’s before looking through the bookshop and Sophie’s for hidden gems, but they always wound up sitting in the gazebo talking about nothing and everything until Lane was forced to run back home.

In the three months that he’d been here, Jess wasn’t exactly what he would call Rory Gilmore’s friend, and yet, according to Luke, she considered him one of her best. He exactly wasn’t sure why he’d made the choice to keep his distance, so he chalked it up to a multitude of things:

One, she had a boyfriend and while Jess had never really considered his feelings for Rory Gilmore, he genuinely hated that tall bag boy she spent all her time with. Seeing them made him feel weird, queasy almost. They were sickeningly sweet, and Lane drove the point home with all her starry eyes and cooing about how cute they were. Jess knew guys like Dean, so in the end he was sure that he was doing Rory a favour by staying away.

Two, he would ruin her. Rory was an intelligent girl, probably one of the most intelligent girls he’d ever met, and she had big goals and even bigger dreams. Her mother, who was nothing like his mother, had done everything in her power to get her into a fancy private school out in Hartford. Jess was happy for her, really. Rory had been talking about that school for as long as he could remember but her voice had always been wispy, almost as if Chilton was a far off, unrealistic dream. But, if anyone could make their dreams come true, it was Rory Gilmore, and she certainly didn’t need a screw up from the lower east side ruining her chances in life.

He’d read enough books to know what boys like him did to girls like her.

Three… Well, he didn’t have a three, but he was sure one would come up eventually along with a four, and a five and a six. Her mother probably would agree, so maybe there was number three, after all.

And yet, she still stormed into the diner on Christmas Eve and told Luke she was kidnapping him for a few hours as if Jess hadn’t spent the past three months avoiding her.

“Put this on,” she said, thrusting a solid pastel pink scarf at him.

He looked at it, then up at her. “No.”

Rory bristled but didn’t cower back. “I meant put it around your eyes! It’s your blindfold, it was the least offensive scarf I could find.”

“Rory—“

“It’s for your first birthday surprise! Please, Jess?” she pleaded, lower lip positioned out further than her top, her blue eyes begging in all their Bambi glory.

He could feel all of the eyes on them though the Diner was relatively empty thanks to the holidays. Rory whined as she moved closer, still handing him the scarf. Jess looked around, frowning as he caught Luke watching them in interest. He ignored the embarrassment creeping up the back of his neck and snatched the scarf from her hand, tying it around his eyes so he couldn’t see anything. Rory clapped in joy and placed her hands on his shoulders to steer him into his coat and out of the diner and to the his top secret birthday surprise.

Honestly, he couldn’t tell how long they were walking for when they reached their destination. Rory cheered once they made it and moved to take off the scarf. Jess blinked as his eyes adjusted to the light of the cold, winter day. They were standing on the old bridge, the same one he came to when he needed to time to himself to think. There was a large white gift box in the middle with a few red balloons tied to the matching ribbon and Rory looked mighty pleased with herself.

“Happy Birthday! Go open your gifts, but read the card first!”

He did as he was told, staring down at the comedic card in his hands that told him he was turning six instead of seventeen. He rolled his eyes and Rory giggled, but on the inside there was a long heartfelt message that detailed how excited Rory was for him to be living in Stars Hollow and how she thought of him every single day and loved talking to him on the phone and worried about him when he was gone. Jess bit the inside of his lip, unsure of what to say or how to react. He’d never had someone like Rory in his life before.

“Is it okay?” She asked tentatively. “Sorry if it’s too mushy, I just wanted you to know how I feel because we haven’t talked much since you moved here and I’ve been so busy with school and Dean, but mostly school, I would never ignore you for a boy—that’s just silly. But I figured since we haven’t talked much, your birthday was the perfect time for me to tell you that I think you’re great, and really special, so smart, honestly. You could probably even go to Chilton if you wanted! You’d do really well there, it was hard for me to adjust last year but I did it and I think you could too. Oh god, what am I saying? You probably don’t want to go to Chilton and wear a dorky uniform. I’m going to stop talking now and let you open the rest of your gifts.”

He couldn’t help the smile growing on his face as Rory rambled on, but he looked down into the box and pulled out a small stack of books she’d tied together with ribbon. They looked old and worn and had that smell Rory was always babbling on about. He turned to look at her again, smirking at the look of apprehension she gave him.

“Thank you, Rory. This is great.”

She grinned then, clasping her hands together as she swung her legs back and forth over the bridge in glee. “I’m so glad you like it!”

“You didn’t have to do this for me. It’s too much. You’re being too nice.”

Rory reached over to hug him then, and he wrapped a single arm around her back. “Best friends are supposed to be nice.”

  


**AGE TWENTY-THREE, NOVEMBER. PHILADELPHIA**

Rory groaned when she woke up on Saturday morning, her back stiff and head pounding. She reached for the bottle of water she kept on her nightstand only to find it empty. She whined, sinking back down into her pillows and twisting onto her other side to poke a sleeping Jess. He grunted at her when she poked his side, shifting away from her in his sleep, but she was relentless.

“Jess, share your water with me.”

“Get your own water,” he mumbled into his pillow, bringing his own blanket up and over his head.

They’d learned the hard way that they couldn’t be under the same duvet lest they wanted to wake up awkwardly pressed together in all the very, very wrong places. It’d taken Rory at least an hour to calm down after it’d happened the first time, her thighs pressed together hard in failed attempt to alleviate her arousal. She didn’t know if he was as horribly affected by her as she was by him, but she was too embarrassed to find out.

“The kitchen is too far away,” she complained, pressing herself into his back as she reached over to grab his water bottle. “Plus, I don’t feel well.”

He flopped over to look at her, eyes bleary. “What’s wrong?”

“My head hurts and I feel achey.”

He grunted, threw the covers off of himself and hopped out of their bed in nothing but his boxers. “Stay here, I’m getting you Tylenol.”

“Aw, you’re such a good friend!” She called after him, silently (and guiltily) admiring the way his back muscles rippled when he moved. His ass was solid, something she’d noticed when she woke up pressed against his back one morning after moving in. She couldn’t wait for him to return, knowing she’d get a full view of the front, his boxers really didn’t hide much.

_Yet another temporary moment of insanity_ , she told herself, unwilling to believe she could really be this thirsty. God, she needed a boyfriend. _But what man would date you once he finds out you’re sharing a bed with another?_ She groaned at her own thoughts, smacking herself in the face with her pillow.

“What are you doing?” Jess asked, staring at her from the doorway of their bedroom.

Rory sat up, pulling the pillow into her lap. “Nothing,” she said quickly, blushing. “I was just thinking about how I hate being sick.” In the head.

“So you hit yourself repeatedly?”

“I’m punishing myself for being weak.” It wasn’t a total lie.

“Huh,” Jess said as he sat on the edge of their bed and handed her the pain killers with a small glass of water. “Okay, well, I put some Poptarts are in the toaster because you shouldn’t take Tylenol on an empty stomach.”

“Thanks, Dad,” she said, rolling her eyes.

Jess shivered. “Don’t call me that, it’s creepy.”

Rory mock gasped, unable to walk away from an easy joke. “Jess Mariano, are you… a _kinkshamer?_ ”

“Rory Gilmore, are you saying you have a _daddy kink?_ Toward _me?”_ He smirked, eyes alight with laughter as he matched her tone. 

“Ew, no!” Rory cried, feeling her cheeks heat up as she popped the medication into her mouth and downed it with the icy cold water. Damn this cold, she’d walked right into that one without so much as thinking about it. “I do not have a daddy kink for _anyone!_ ” Paris had always said she’d only liked Logan because he reminded her of her father, and that was something that Rory just was not ready to accept or remotely acknowledge.

Jess raised a single eyebrow at her.

“I don’t! I’m just as likely to have a daddy kink as you are to have a mommy kink, okay?”

Jess scrunched up his nose with a disgusted scowl. “Okay. I believe you.”

“Thank you.”

He moved to feel her temperature with his hands, cupping her jaw in one as he felt her forehead with another. “You’re warm,” he said seriously, all signs of their previous joking gone. “You feeling okay aside from being achy and the headache?”

She nodded dumbly, leaning into his touch just as he pulled away, standing right in front of her. She made sure to try and keep her eyes focused on his, but she glanced down without meaning to and took in the bulge protruding from his boxers. He wasn’t hard, but he didn’t seem completely flaccid either. She snapped her eyes right back up to his face, determined not to stare or make him feel uncomfortable in his own space.

If he’d noticed where her eyes went at all, he didn’t let it show. “Okay. Rest up. I’ll bring you your Poptarts.”

“You’re being too nice,” she told him, pressing her thighs together underneath her covers as the dull ache between her legs unwillingly returned.

He shrugged at her just before he left the room. “Best friends are supposed to be nice, right?”

She flexed her thigh muscles, pressing them tighter as she forced out a smile. “Of course.”

  


**AGE TWENTY-THREE, DECEMBER. PHILADELPHIA**

“So, you’re sexually attracted to Jess,” Paris said, a little too loudly for Rory’s taste.

She looked around the coffee shop, making sure no one she knew was around. Jenn was working today, but she was on cash, which thankfully was far away from Rory and Paris’ table.

_“Yes,”_ Rory whispered, face burning in shame. “It’s awful! Last month I looked at his crotch _while_ _he was talking to me!_ ”

Paris shrugged as if she didn’t see the problem. “So? Women need to be more assertive in their sexual needs. Men ogle us all the time, why can’t we ogle them, huh? He’s single, you’re single, just bang it out already. I’m sure he’s good at it. I, for one, am just glad you’re acknowledging how badly you’ve wanted to fuck him since you were seventeen.”

“I did not want to... I didn't want to have sex with Jess at seventeen. I was very loyal to and happy with Dean. Besides, Jess is my best friend, I shouldn’t be looking at him that way. I hate that I looked! The worst part is, I was practically wishing for him to turn around so I could look. God, if you could’ve heard my thoughts… they were shameful. Straight up sin! And just because men ogle us, doesn’t mean we should ogle them back.”

“Please,” Paris waved her words away like an annoying fly. “You, my friend, are blind. Jess ogles you constantly.”

Rory opened her mouth to argue, but faltered when she fully processed what Paris was saying. “He does? No, he doesn’t.”

“Trust me, he does.”

“How do you know?”

“I know a dog in heat when I see one,” Paris spat. “He may as well follow you with his tongue hanging out panting! Didn’t you say that he was saying some sexual shit to you last weekend at some party that I was conveniently not invited to?”

“You were at school, Paris. Harvard, remember? It’s in Boston, which is kind of not close to here.”

“Excuses,” Paris chided with a sharp glare. “Tell me what Kerouac said.”

Rory sighed, shoulders sagging in defeat. “He… did say some sexual things, yeah, but I mean he was drunk. He hit a mason jar with a hammer and yelled about how he hates the system. I think it’s safe to say he was a little out of control.”

Paris muttered something under her breath that Rory couldn’t quite catch but she was sure she heard the words _‘foolish’_ , ‘ _hipster’_ and _‘blackmail’_. She stirred her spoon around in her tea mug and looked sharp again just before she said, “So, what _exactly_ did he say? Or are you too big of a prude to tell me? You know, women need to be more open about their sexuality. I didn’t hide a thing from you at Yale.”

“I wish you would’ve,” Rory mumbled into her coffee just before taking a sip. She took a deep breath and fought against the shame and embarrassment creeping up her spine as she recalled Jess’ words. “He said… he does _a lot of things for me_ , but he whispered it into my ear while at the table so that no one else could hear him and then… He asked if we were going to go to bed together. I mean I guess it wasn’t that sexual but you should’ve heard the way he said it. Am I just crazy?”

“No, you’re not crazy. He said all of that and you didn’t fuck his brains out!?” Paris demanded to know, slamming her hands down on the table so hard that it called the attention of others around him “You know what? I take it back! You are crazy. That’s practically _‘I want to fuck you all night long’_ in Jess speak! You had the perfect opportunity and you _wasted_ it!”

Jenn was looking at them now, confusion etched between her furrowed brows. Rory smiled back and gestured for her not to worry about it. She turned back to her best friend with a tight lipped smile and wide eyes. “Can you maybe not embarrass me? I come here a lot…” Rory grit through her teeth, and Paris softened for a moment but quickly became all hard edges once again.

“I can’t believe you didn’t fuck him,” she scoffed, though her words were much quieter now. “You just don’t love yourself.”

“I just don’t want to ruin our friendship,” Rory said, blushing.

Paris rolled her eyes. “You know what’s going to ruin your friendship? You not fucking him. You’re just gonna stare at him and hope to god he can smell your pheromones or something? Maybe rub yourself up on a fence like a dog in heat and suffer in silence then guess what? He’s going to move on! Yep, get another girl he can fuck at will because he’s twenty-three and hot. And you? You’re going to be left in the dust, forced to move out once some other girl sinks her claws into him and forces him to kick you out of the apartment. You’ll go back to Mr. Greene’s shitty basement, but hey! Maybe he’ll let you keep a couple dozen cats.”

_ “Paris!” _

“Is that what you want, Rory?” Paris hissed, leaning forward with her eyes narrowed into slits. “Huh?! Is it!? You want to be a pathetic cat lady forever with no one to love you except your furbabies? Why settle for that when you could be with Jess, who you love. Or would you prefer the pathetic existence I've laid out succinctly?”

“…No…” She really didn’t know what she wanted, but she knew she didn't want to be alone with a dozen cats. And what did she even want from Jess? Was it just sex? Or something more? Would she even have the time to find out if Paris was right about another girl getting to him first? “That’s not what I would prefer.”

Paris slumped back in her chair looking satisfied as she crossed her arms over her chest.. “I didn’t think so. You better do something about it before that other girl, what’s her name? The one you said was all over him last weekend.”

Rory bit her lip. “Val?”

“Yeah. You better hurry up before Val beats you to it.”

“I think they’ve already slept together, honestly… She just seemed too comfortable with him, you know?”

Paris threw her hands up then. “Great! So she’s already experienced and knows what he likes in bed. You’re lucky you have one thing going for you that these other girls don’t or else I'd tell you to give up.”

“What? What do I have that they don't?” Rory asked, genuinely curious.

Paris huffed loudly as if Rory had just asked the most stupid question. “He's obviously in love with you. God, you really are blind.”


	2. Chapter 2

**Notes for the Chapter:**

> Yeah, so in this AU Jess had a high school sweetheart who wasn't Rory. Avery is a character who is near and dear to my heart, so I hope you all like her despite her history and current relationship with Jess. Just know she's not really the kind of girl who lives for drama, so there's not going to be some big love triangle or anything. 
> 
> Anyway, I hope y'all like it! Don't forget to leave me a comment telling me all your thoughts and feels.

**AGE SEVENTEEN, JANUARY. STARS HOLLOW**

Stars Hollow High was nothing like his old high school back in New York.

For one, Jess had never seen a classroom filled with so many white people in his entire  _life._ The town seemed to find pride in their squeaky clean reputation, which Jess knew came from underhanded racism and prejudice, even if no one else saw it. There was a reason he could count his peers of colour on one hand, and after growing up in the Lower East Side this whole white-washed society thing seemed a little more than off-putting. He'd known more Black and Latinx kids than he did white growing up; his closest friends and neighbours had all been people of colour but Stars Hollow seemed to have a completely different definition of diversity. Maybe Taylor should talk about  _that_ in the next town meeting.

His frustration with Stars Hollow came alive in one of his personal essay’s in an anecdote when he'd thought that _maybe_ his teacher, Mr. Ramesh, would appreciate it. But, now, as he was sitting in Mr. Ramesh’s office, his heart in his throat, he started to regret the whole thing. Maybe Mr. Ramesh didn’t agree that Stars Hollow was repressive and stifling; maybe he didn’t seen an issue with so many white people around, and maybe Jess had overstepped his boundaries in thinking that one of the only teacher’s of colour at this high school would see what he sees.

Jess drummed his fingers on the chair as he waited for Mr. Ramesh to return from talking to a colleague. He could hear their voices outside the door, but he couldn’t hear exactly _what_ they were saying—not that it mattered, he doubted it had anything to do with him anyway.

Finally, Mr. Ramesh returned, his office door squeaking as he forced the door open. This school was not only white, but it was cheap and falling apart. Jess kept his eyes forward until he saw Mr. Ramesh.

“So, Jess,” Mr. Ramesh started, his hands folded neatly atop his desk, “do you know why I called you in here?”

“My paper?” He asked, barely able to get the words out.

Mr. Ramesh nodded and pulled it out from a locked cabinet in his desk. “I, of course, have not had the time to give these back in class yet, but I like to talk to my students about the more _exceptional_ papers I receive at the beginning of term. Your writing is phenomenal for your age, has anyone ever told you that?”

Jess took in a shallow breath, heart thumping wildly for a whole set of different reasons now. He was being _praised?_ This had never really happened to him before. The Lower East Side was _filled_ with what white teacher’s referred to as “troubled youths” and they were, of course, _always_ students of colour. His friend, Alexis, had always ranted about they put those labels on the most dangerous of Black and Brown kids without so much as looking at the white kids. It was an easy racist trap to fall into, she said. To assume that every child of colour is more dangerous and needs greater attention and more rehabilitation; it wasn’t equality, but rather another form of systemic prejudice.

It’s how Liz’s neglect went unnoticed for so long, and how Alexis had child services take her away despite her mother being kind, devoted and more loving than Liz had ever been.

“Um, no,” Jess forced himself to say, not wanting to seem rude.

“Thought so,” Mr. Ramesh noted. He slid Jess’ paper toward him with a swift push and a smile. “You are exceedingly bright, Jess. I was warned that you could be a little standoffish by Principal Merton and the student councillors here at this school, but no one told me what a talented young man I’d have in my classroom.”

Jess thumbed through his paper, taking in all the check marks and positive comments littered in the margins. Beside his personal anecdote, Mr. Ramesh had written a long comment that detailed his agreement with Jess’ assessment and how _important_ he thought it was that Jess was aware of social inequality at such a young, ripe age. The burst of pride he felt was an odd feeling, but not an unwelcome one.

“Thank you, sir.”

Mr. Ramesh grinned. “I don’t know if you know this about me, but I run a creative writing circle after school. It’s small, very small actually. It consists of just myself and my daughter, but we have fun. I was reading your essay and I couldn’t help but feel as if your writing flows like prose. Have you ever considered being a writer?”

“No,” Jess croaked, still in shock and feeling as if he were on auto-pilot.

“You should think about it. I think you’re very well suited to it.”

He didn’t know what to say or how to react, so he just put his paper back down onto the desk. “Maybe.”

Mr. Ramesh looked like he was ready to say something, but he ripped his eyes away from Jess to look behind him, curiosity etched in his brow. Jess twisted back to see what exactly his teacher was staring at just in time for the door to squeak open, revealing a petite girl with long black curly hair and radiant medium brown skin. Jess had seen her walking the halls sometimes, though he’d never talked to her before and they didn’t seem to have any classes together. He didn’t even know if they were the same age.

“Sorry, I didn’t mean to interrupt,” she said, looking between Mr. Ramesh and Jess, “I just wanted to know if I should go home or if we were going to have a circle meeting…?”

Suddenly everything clicked, and Jess could see the resemblance between the two.

“That’s all right, Avery. I was actually just talking to your peer about our little meetings, wasn’t I, Jess? Trying to convince him to join us one day.”

“Oh, really?” Avery asked, her big brown eyes locked onto Jess’ own. “You write?”

Jess gave her a one shoulder shrug. “Not really.”

She looked at him oddly but smiled all the same, and Jess felt his pulse spike.

“I’m Avery,” she said, now at his side with her hand extended for him to shake.

“Huh. So I’ve heard,” Jess quipped back with a smirk, grasping her hand.

“Do _you_ have a name?” She asked, fighting back the smile pulling on the corners of her lips.

Jess nodded, remembering that her father was in the room. “Jess. Jess Mariano.”

 

**AGE TWENTY-THREE, JANUARY — NEW YEARS DAY. PHILADELPHIA**

“Remind me to never drink on New Year’s Eve again,” Jess complained, flopping down on the couch next to Rory, his arm casually thrown over the back of the chair. “Why the fuck is it a social thing to _start the new year off right_ by getting shitfaced and then _actually_ starting the New Year with a god awful hangover? That’s like… the worst idea ever.”

“Sheer irony,” Rory said, handing him an unopened bottle of water from the coffee table.

He grunted his thanks at her, popped the cap off and started to chug. When he felt satiated he twisted the cap back on and held the beverage in his lap. “Hey, where’s Lane anyway? I think she went harder than me. Did she die?”

“Nope, no death. I think she just fell asleep in Chris’ room.”

Jess blinked at her. “Chris’ room?”

Rory shrugged. “They were flirting pretty intensely at the bar from what I could see. You were probably too drunk to remember this but you were kind of egging them on to _do stuff_.”

“Wow, I’m a dick.”

“I’ve been saying that for years,” Matt said, suddenly appearing in the living room. His mop of brown hair was a complete mess, he was decked out in silky Santa boxers that Rory had bought him for Christmas and a Rudolph robe—glowing nose and all.

“Don’t worry, Lane wouldn’t _actually_ do anything. Y’know, because of the whole no-sex-before-marriage thing.”

“I’m not worried,” Jess said easily, waving the whole Chris-Lane thing away. “Even if she did do something, it’s none of my business. No matter how much drunk 2007-Jess may have disagreed. He’s dead now. 2008-Jess is here and he is regretting _so much_ already. I think I need an Advil.”

Rory smiled at him, but it quickly faded once Matt left the living room to go make everyone breakfast and Jess leaned to ask,

“I didn’t… do anything inappropriate last night, did I?”

Jess knew himself well enough to know that he got more than a little rowdy when he crossed a certain alcoholic threshold. He had a tendency to break things and flirt relentlessly, and most of the time he always flirted with Rory. There were one too many sexual innuendo’s he could remember throwing her way each time they drank together but it's not like drunk Rory was much better. Alcohol seemed to be her very own _Felix Felicis_ and she had a tendency to come onto him when drunk. Paris and Lane had an on-going bet about whether or not the two of them would wind up fucking while smashed.

“Um... Well… No. I mean… N-not really? Some people might think your actions were inappropriate maybe, b-but, y’know, in the grand scheme of things they don’t quite seem _so_ bad…” Rory stuttered, her answer a little to cryptic and her voice a little too nervous for Jess’ taste.

“ _Fuck_ ,” he breathed, preparing himself for the worst. He leaned back and studied her for a moment before asking, “What’d I do?”

“Nothing bad to anyone, really! I’m sure the recipient actually really enjoyed what you did it was just kind of awkward for others… mainly me, because I try not to see you in that light but you kind of make it difficult and… No, what am I saying? It’s fine. It’s fine, really.”

“ _Rory. What_ did I _do?_ ”

“First let me preface this story by saying that we _all_ did things last night that we maybe shouldn’t have and yours was actually one of the least horrible offenses that I happened to witness. Matt actually broke a thousand dollar bottle of champagne… Chris and I had to help him pay the bill.”

He raised his eyebrows at that, but he figured he could get the details from Chris later. “Tell me what happened.”

“Well, it started when Makes Me Wonder by Maroon 5 came on and he started to sing it as if Riley were in the bar—“

“No, no,” Jess said waving the story away. “Not that. I definitely want to hear about that later, but I meant tell me what happened with me and you last night.”

“Oh! That story actually has more to do with Avery.”

“Avery?” Jess asked, confused. “Avery Ramesh?”

Rory nodded. “That’s the one.”

“I thought I dreamed that,” Jess said, scrubbing hard at his scalp. “She was actually there?”

“She was,” Rory confirmed, sounding a little somber (the way she always did when Avery was brought up). “She called you to say she was in Philly visiting her little sister at college and that she didn’t want to spend New Years alone in her hotel and she’d heard from her dad that you were living out here and somehow she tracked you down.”

“Huh.”

“You were already drunk when she called.”

Jess nodded, feeling like what Rory was saying made sense. “Interesting. So, what, did I hook up with my old high school sweetheart or something?”

“Kind of.”

“Elaborate.”

“You kissed her at midnight… well, more like almost had sex with her against a wall outside the bar. I stumbled upon you because I wanted to wish you a Happy New Year. For some reason you felt _very_ guilty about it and kept chasing me around the bar to apologize.”

Jess blinked, finally having reached the point where his drunk actions made no sense to his sober self. “Were you upset with me or something?”

Rory fiddled with the hem of her shirt and avoided his gaze. “Um, a little bit… yeah”

“Okay. How come? I honestly don’t remember anything, Rory. You gotta help me out.”

She shrugged a little, chewing at her upper lip.

Jess leaned forward to shake her thigh a bit. “Rory, come on. You can tell me.”

“It’s stupid.”

“I’m the king of stupid.”

He watched as she waged an inner battle with her thoughts, cheeks red as the wheels turned round and round in her head. Jess kept his hand on her knee to let her know he wasn’t about to judge her, squeezing it for an extra dosage of support. She looked up at him with a newfound resolve in her eyes and she released her lip to lick her bottom one.

“You promised not to let me spend New Years alone and then Avery called and you pretty much abandoned me. I was upset with you because you broke your promise.”

“Shit… I suck at keeping promises I made when drunk. I'm sorry.”

“I know. I already know that about you, and honestly that’s why I’m embarrassed that I was upset instead of being mad at you. It was stupid. You deserve to have fun on New Years, even if that means having sex outside against a wall with your high school sweetheart. It just..." She sighed. "It was stupid of me to be upset with you.”

“Listen, if anyone was stupid last night it was _clearly_ me,” Jess argued, squeezing her knee a little tighter. “This was your first New Years without Logan, and I’m sure I made that promise to you fully knowing that. It’s just that drunk Jess is, well... he's an asshole and apparently he’s much more stupid than I originally thought. I tried to sleep with my old high school girlfriend? _Seriously?_ What the fuck is wrong with me?”

Rory shook her head, smiling a bit. “Nothing’s wrong with you. I went back to Dean that one time when Logan and I _'broke up'_ , remember?”

“Yeah, that _was_  pretty stupid,” Jess agreed, earning him a playful glare from Rory. “Look, can I make this up to you somehow?”

“No, that’s not necessary. Besides you have a lunch date with Avery in an hour. I promised her I’d remind you.”

Jess groaned, leaning back into the couch cushions, his hand now gone from Rory’s knee. “Friends don’t let friends make dates with their exes while _drunk_ , Rory! I’d never let you do that if Dean or Logan came around!”

“Sorry,” Rory shrugged, “but you can’t really tell drunk Jess anything. He just tells you he’s an adult and can make his own decisions.“

“I hate drunk Jess,” he said and Rory simply laughed.

 

**AGE SEVENTEEN, JUNE. STARS HOLLOW**

Rory was getting really tired of waiting for Jess to call.

They’d made plans to go out and explore Hartford almost two weeks ago, but Rory had to cancel last weekend when Dean surprised her at home with tickets to a movie she’d really wanted to see. Jess hadn’t seemed to mind that she needed to cancel, answering her with a general nonchalantness that always managed to get under her skin. Luckily, she was free this weekend with Dean working long shifts at the market and Lane off doing something with her mom. Even Paris wasn't being annoying for once in her life, so Rory had all the free time in the world to hang out with Jess, but their 'friend date' was supposed to start twenty-minutes ago and she hadn’t heard from him at all.

“Hey Babe, still no word from Jess?” Mom asked just after walking through the front door with an array of food from Al’s.

“Nope,” Rory said, keeping her eyes an old ‘I love Lucy’ rerun on TV. “No word at all.”

“Maybe he’s distracted by that super pretty girlfriend of his.”

Rory frowned, twisting on the couch to face her. “Jess wouldn’t blow me off for Avery.”

“Hon, you _literally_ did that to Jess last weekend.”

“That’s not fair! Dean surprised me and I couldn’t let him down.”

Mom shrugged, dropping the bags of food onto the coffee table. “What if Avery surprised him?”

“He’d call and tell me so.”

“Jess doesn’t even own a cellphone, babe.”

“Then he’d swing by.”

Mom raised her eyebrows then. “You think he’d swing by to tell you he’s too busy for you? Boy, you really do think highly of him.”

“Mom, stop. I'm sure he's just running a little late.”

She raised her hands in the air, signalling defeat. “Okay, okay. Sorry,” she said just as the phone began to ring.

“I bet that’s him now,” Rory said, feeling smug as she pushed herself up off the couch. “Hello?” She answered, feeling peppy.

_“Rory, hey.”_

“Jess! Hi,” she greeted, sticking her tongue out at her mom. “I know you’re running a little late, but I think we can still make it to the record shop before it closes.”

Jess paused for a moment. _“Uh, yeah… about that. Could we maybe reschedule?”_

“Oh,” Rory said, heart sinking. “How come?”

_“It’s just that Avery’s mom came into the diner and she asked if I’d like to go out to her art show and it’s happening at nine and … I mean, If you really want to go tonight I can just say no. I just figured I'd call and ask.”_

Rory nodded, though he couldn’t see her. “No, no! That’s okay, Jess. That sounds fun, you should go. We can reschedule.”

_“You're sure?”_

“Completely,” Rory lied, forcing a big, dumb smile onto her face (more for her mother than anyone else).

_“Maybe tomorrow?”_

“Yeah. Tomorrow’s good.”

_“Okay. Bye, Rory.”_

“Bye, Jess. See you tomorrow.”

When she hung up, her mom was staring at her with a look that said _I told you so._ “Well, at least we can have a movie night?” Mom offered.

“I should use this free time to study.” Rory huffed, slamming the cordless back down on the base before she shut herself in her room.

 

**AGE TWENTY-THREE, JANUARY — NEW YEARS DAY. PHILADELPHIA**

Seeing Avery Ramesh in Philly while completely sober was a very, very weird thing for Jess.

She hadn’t changed much, really. She was still petite and slim with long curly hair, though she’d dyed it a deep auburn shade that genuinely seemed to suit her brown skin tone. At the ripe age of twenty-two, she wore more makeup than she’d ever had in high school but Jess didn’t necessarily think that was a bad thing. There was a natural, fresh faced kind of quality to her make up look that he kind of appreciated.

He recognized the notes of her signature perfume when they hugged—cedarwood, roses, and spice. He’d smelt like this for hours after spending too much time with her in the past. Just being around her in the right frame of mind seemed to bring up old feelings that he didn’t even know he still had. He’d put up a good front in front of Rory, but Avery would probably _always_ pull out something in him, even when he didn’t want her to.

“So, Jess, how are you?” She asked just after taking her seat at their table.

“Good. Kind of hung over… Look, I just want to be transparent and say that I don’t remember much from last night.”

Avery nodded, beautiful smile in place. “I didn’t think you would. It’s okay, Jess. I’m not here looking for a ring.”

“You never were. That was always why I liked you.”

She laughed, still as pretty a sound as he remembered. “Still have a phobia of commitment, huh? Isn’t that why your last girlfriend broke up with you?”

“Hey, I dated you for _three whole years_. That’s a pretty big accomplishment. Dinah was… a little too invested, honestly.”

“Well, we’re not kids anymore. People date to find _The One_ and get married nowadays, though I personally don’t see why.”

“We’re still young,” Jess said, leaning forward to grab a menu from the middle of the table. “I just don’t see the need to settle down anytime soon. If I never get married I’ll be happy.”

Avery hummed in agreement. “I remember Rory saying she almost got married a year ago or something like that last night. Forester wound up proposing? I know we always joked bout that, but you’d think he’d have learned after his horrible, rushed marriage to Lindsay.”

Jess laughed as he flicked through the menu. “No, it actually wasn’t Dean,” he said, looking up at her. “It was her Yale boyfriend. Logan Huntzberger.”

“Huntzberger,” Avery repeated, trying to place where she’d heard that name before. “Like… the newspaper family?”

“Yeah. Exactly them.”

“Wow. Seems like she did well for herself in the romance department after Dean. How come she didn’t marry him? You’d think they’d be a journalistic power couple together or something.”

“I think she kind of wanted to be that with him too. But, in the end, I guess she just wasn’t ready to take that step. She still loves him I think, but he said it was all or nothing and walked away when she said no to marriage.”

“You sound like you don’t like him very much.”

Jess shrugged a little, looking back down at the menu. He’d tried, for Rory’s sake, to befriend Logan, but it’d never taken off. They had their moments of cordiality and sometimes it seemed like they _could’ve_ been friends, but with all the shit Logan put Rory through during their relationship, Jess just didn’t have it in him to play nice.

“He was kind of a jerk.”

“You used to say the same about Dean.”

“What can I say? The girl likes jerks.”

“Not always,” Avery said with a strange look in her eye but Jess decided not to take the bait; he had a good feeling he knew what she was getting at and that just wasn’t a conversation he wanted to have right now. He and Rory were complicated and he didn’t need to start justifying it.

They lapsed into silence, the both of them looking over the menu before their waiter came to take their order. Jess ordered a a hefty breakfast meal—three eggs, sausage, bacon, toast and a pancake with a side of orange juice. Avery was far less ambitious with an order of salmon eggs benedict and a hot chocolate.

“You look good if I haven’t said that already,” Jess offered once their waiter was gone.

“I gathered you thought so when you kissed me last night.”

Jess snorted. “I could’ve just been thinking with my dick.”

“You’ve never been the type to _just_ think with your dick, Jess.”

He smirked, knowing she was right. “Well, still. I wanted to say you look good, so, I reiterate: you look good.”

She sat up a little straighter, smiling with her teeth. “You look good, too.”

“How’s your dad?”

“He’s doing well, actually. He left Stars Hollow High to teach at a college level and he’s loving it. He misses you, too. Talks about you all the time, even gave me a copy of your book—congratulations on that by the way. Dad was very touched by your mention of him at the beginning.”

Jess ducked his head, feeling bashful. “Maybe I’ll pay him visit when I go back to the Hollow.”

“He’d like that.”

They spent the rest of their “date” catching up each other up on the past four years that they’d been apart. Avery talked of her mother and her little sisters experiences at college, voice wispy with longing as she talked about her own graduation day and how hard microbiology had been as a major. Jess told her all about Matt and Chris and Truncheon and how they’d come together to create something that seemed totally impossible to him at the age of eighteen. He talked of Rory, Lane and Paris, and how they’d managed to keep their friendship alive even after all these years. And when they’d finished their meal, they argued over who would pay and in the end Avery won out with little teasings about him being a starving artist.

“It was so good to see you,” Avery said, once they’d paid the bill and stepped out into the cold. “I really missed you…”

“This doesn’t have to be goodbye if you don’t want it to be.”

Avery stared up at him, sucking her bottom lip under her top teeth. “I don’t want to cause problems.”

“How could you _ever_ cause problems?”

She looked down at her boots with a small laugh. “I caused problems last night between you and Rory.”

Jess shook his head. “No, you didn’t. _I_ promised Rory that I’d spend new years with her because this was her first one without Logan, but then I got drunk and you showed up and…” He took a deep breath, trying his best to explain as he took a step closer to her. “You always were the perfect distraction. Trust me, she’s not mad…”

“Don’t do that.”

“Do what?” He asked, taking another step forward.

“ _That,_ ” she breathed, her curls flying as she shook her head at him and backed away a bit. “You’re hard to resist, you know. It’s how I wound up against a wall in public last night.”

“Well,” Jess said, grinning wolfishly as he reached for her hips and gently pushed her back against the storefront wall, “we could do a replay of last night… I’ve gotten _much better_ at the whole sex thing over four years and you didn’t even get to find out.”

“I think I’d greatly prefer you showing me in a bed,” she whispered right before he kissed her.

 

**AGE SEVENTEEN, OCTOBER. STARS HOLLOW**

The diner was busier than usual and Jess was crankier than usual.

He’d stayed up all night working on his paper that he _had_ finished earlier but lost completely when Avery’s computer crashed on him. He kept telling Luke they needed their own in the apartment upstairs so he could stop mooching off of others, but Luke seemed to be firmly against the idea when the library, Rory’s house and Avery’s house existed. In the end, he wound up working on his midterm at the Ramesh’s until almost three in the morning and crashed in Avery’s bed until Luke called incessantly at six to make sure Jess came back home soon enough to get ready for school.

The school day had lasted _far_ too long and he’d considered skipping and taking a nap on the bridge, but it was too close to the premises and someone would be bound to catch him and tattle to Uncle Luke. He wound up suffering through his exhaustion in the end, but caught a few winks of sleep at lunch with his head laying in Avery’s lap. Still, it hadn’t been enough to improve his mood in the slightest.

Luke had him working a short shift after school, making sure to leave him enough time to do any school work he had. Unfortunately, the plucky citizens of Stars Hollow were being extra annoying today, especially Kirk who kept returning his dishes with some sort of stupid complaint.

“Kirk, eat your damn eggs or I’m going to make you wish you were never born,” Jess snarled and that had been enough to get Kirk back in line.

At around six, Lorelai came in alone with talks of how Rory was out on a date with good ol’ Dean, and Jess wanted nothing more than to bash his face into a wall. He’d managed to tune her out eventually, thankful for when she’d started her typical flirtation with his uncle in front of all his patrons. He could feel her eyes on him every so often, following him around the diner as if she wanted to say something, but she held her tongue until Avery came and went, greeting him with a quick kiss as she ordered a chai latte.

“You guys are kinda cute,” Lorelai said with a teasing grin. “Kissing over the counter and all. It’s precious.”

“Uh huh,” Jess said, refilling her coffee cup.

“You know we’re having a big birthday celebration for Rory this weekend.”

“I know. I was invited.”

“Yeah,” Lorelai said sounding peppy, “but you know who _wasn’t_ invited but _should_ be invited?”

Jess rolled his eyes. “Is it Barney? Maybe Spongebob? Rory _loves_ Spongebob.”

“Avery!” Lorelai answered, almost as if she hadn’t heard any of Jess’ previous snark. “Dean’s gonna be there, so it might be nice for you and Rory hang out with your _significant others_ together.”

“Lane will feel left out.”

Lorelai blew a raspberry and waved his concern away with both hands. “Lane is a strong, independent woman! She will be just fine.”

He doubted that, but didn’t voice it. “Why do you want Avery to come?”

“I dunno,” Lorelai shrugged loosely. “Just thought it’d be nice. You two have been dating a while and Rory was saying she’d like to get to know her better, so…”

“She never said anything to me.”

“Yeah, well, you’re not her _best friend._ ”

Jess stared at her then. “Except I am.”

“Mother-who-is-also-best-friend  _totally trumps_ best-friend-who-happens-to-be-a-very-silly-boy. She tells me more things, duh.”

“Okay,” he said easily, unwilling to fight over something so stupid and probably true in the Gilmore world.

She took a big gulp of her coffee before asking, “So, will and I see you and Avery at the big bash then?”

Jess shrugged. “Maybe.”

“That’s probably as good of a yes as I’m going to get, huh?”

“Yep.”

 

**AGE TWENTY-THREE, JANUARY. PHILADELPHIA**

Jess hadn’t come home after his lunch date with Avery, and while Rory had definitely expected that to happen it still stung all the same. She’d distracted herself by hanging out with Matt, Chris and Lane at the loft. They’d had a typical Gilmore Girls movie marathon with a ton of food and candy, but it felt _wrong_ because Jess was missing. It didn’t help that Chris and Matt were both acting like giggly idiots over all the possibilities of what Jess and Avery were doing. Only Lane really seemed to catch onto to Rory’s true feelings, and she gave her friend a sympathetic glance every time Matt made a joke about Jess’ dick in a box.

“Well, look on the bright side,” Lane said pulling the covers away from Jess’ side of the bed. “Now we get to have a slumber party in your room! Chris is cute, but boy does he ever snore.”

Rory smiled, trying to think of all the positives this New Year would bring. “I know, sometimes I hear him through the walls.”

Lane chuckled and crawled into the covers just after Rory. They both stared up at the ceiling once Rory switched off her bedside lamp.

“I’m sure they’re not going to get back together,” Lane offered after a few minutes of silence.

Rory didn’t respond, too unsure of what to say. Paris’ words from their last meet up played over and over again in her head, beating her down. She didn’t want to think about it anymore. The idea of Jess sharing a bed with someone else tonight was making her sick, and she knew if she talked about it with Lane that she might cry. It was just easier to pretend to be asleep.

Early the next morning, Jess returned in the same clothes he wore out but he didn’t look any different and he especially did not look shameful. Chris and Matt hooted and hollered, punching him in the arm and being their typical gross selves when it came to their friends and sex. Jess looked somewhat smug, but he mostly kept his face impassive. Rory decided it was better not to talk to him in fear out of what he might say.

They all saw Lane off and wished her a safe drive back home to Stars Hollow. She’d planned on staying longer until she’d received a particularly damning message from her mother demanding her return. Rory hugged her friend tight, not wanting to let her go, but she was forced to after Lane joked that she couldn’t breathe.

“Come visit again soon,” Jess said, giving Lane a quick one-armed hug. “Philly’s better with you in it.”

“Aw! That’s so nice!” Lane grinned. “I want everyone to remember this moment.”

Jess snorted, rolling his eyes. “You say that as if I’m never nice to you.”

Lane hugged him again with a short laugh. “I’ll see you soon, Mariano.”

Chris and Matt said their goodbyes as well, Chris lingering around the longest and bidding Lane a farewell with a quick peck on the lips that had Jess raising his eyebrows in interest.

“So, you and Lane, huh?” He asked as they all made their way back up to the loft from the garage. “I called it.”

“She’s a cool chick!” Chris said, sounding slightly defensive.

“The coolest,” Jess agreed.

The four of them fell into their natural rhythm once Lane was gone. Jess hogged the desk in the living room to edit some manuscripts, while Matt and Chris got to work on the zine’s January issue. Rory was able to avoid them by getting ready for work as she had to be in the office by ten.

Work was a little hectic as her editor, Sandra Keaton, was stressed out and ranting about how this years Metro had to be one hundred percent perfect. Sandra handed out everyone their weekly assignments and practically shouted for everyone to get to work; she’d promised if anyone turned in a crap article that she would _personally_ rip them a new one.

Normally, Rory didn’t worry too much about her by-lines, but Sandra had called her out more than once during the day for seeming distracted. Her thoughts were, unfortunately, on Jess and Avery, and she didn’t know what to do or how to fix it, but she was more than certain that she could not let a boy come between her and her dream job.

By the time she’d finished work, she was determined to sit Jess down and have a real, serious talk with him.

 

**AGE SEVENTEEN, OCTOBER—RORY’S BIRTHDAY. STARS HOLLOW**

If there was one thing Jess hated, it was socialization.

It wasn’t that he disliked the people at Rory’s party (though a few of them definitely knew how to get on his nerves), it was just that he had some serious social anxiety issues. Talking to people and making friends didn’t come easy to him, and he wasn’t the Town Prince to match Rory’s Town Princess title. When people tried to talk to him, he was always kind of standoffish and rude without necessarily _trying_ to be. He wanted to be friendlier, but it was hard in a town where everyone judged you in relation to others.

Of course, Jess’ main competition was Dean Forester, and it had been the moment he stepped into this god forsaken town. Yes, living here had been his own idea and he’d come willingly, but really Stars Hollow was just the lesser evil in comparison to his shitty mother. There were good things about this place, but they were far and in between, really.

The whole night people had been gushing over how gentlemanly Dean was and how he was _so great_. Babette had even said something about how Jess could stand to learn something from Dean, and all Jess could do was scowl and say, “Yeah, I’ll get right on that.” The worst part of everything was the fact that Dean somehow thought it was appropriate for them to be _friends_ or something. He kept trying to talk to him and see if they had anything in common, but at the end of the day? They didn’t and Jess was quick to tell him as such.

“Look Dean, I get that Rory’s your girlfriend and whatever, but just because you’re dating her doesn’t mean that _we_ have to be friends.”

Avery told him that he was being a little harsh, but she agreed that he and Dean Forester were not two people she could imagine having a genuine friendship.

He spent the rest of the party on the couch, Avery tucked into his side as they people watched. They murmured to each other quietly and stole a few kisses, but Jess tried to keep things PG knowing Rory hated the way he and Avery had a tendency to get kind of hot and heavy. Still, he kept his hand on his girlfriends thigh, stroking it every so often and feeling an odd surge of pride whenever she’d start to wiggle in her spot and begged him to stop.

The party started to wind down after Rory cut her cake and opened up her presents. He'd given her The Sun Also Rises as a joke, and she'd huffed until he'd handed her another bag with a vintage denim jacket inside that'd cost him a pretty penny.

Avery fell asleep on his shoulder just as everyone started to clear out and he shook her awake with the promise to walk her home. Rory walked them to the door with a shy look and thanked Avery for coming.

“It was nice to talk to you more.”

Avery gave a soft, sleepy smile as she slipped on her shoes and jacket, holding onto Jess to keep her balance. “You too.”

Jess dropped his girlfriend off on her front porch with a kiss and a promise to see her later and made his way back to Rory’s to help her clean up. Dean was still there, compiling paper plates into a garbage bag that Luke had given him and Jess moved into the kitchen to help but was quickly shooed away by Lorelai. He stepped into Rory’s room to find her sitting on her bed surrounded by all her gifts looking morose.

“What’s wrong, birthday girl?”

“Jess!” She stood up quickly to give him a hug. “You came back.”

He held onto her for a moment before letting go with a smirk. “Someone’s really happy to see me even though I was literally  _just here_.”

“Yeah, well,” she looked down, suddenly shy. “I feel like I haven’t really seen much of you lately. You’re always with Avery, or I’m with Dean, or we’re both busy with studying… Even when we’re in the same room it feels like we’re apart.”

“I get it.”

She smiled a little, though it was watery. “I like Avery. She seems nice. I didn’t know her very well when I went to your school, she’s younger than us right?”

“By a year.”

“Thought so,” Rory said softly. “She’s very pretty.”

“She is.”

“And her parents like you?”

“They do, yeah. Shocking, I know. I'm not exactly bring-'im-home-to-the-parents material. But her dad's my english teacher and he likes me so,” he shrugged. "Personally, I think he's a little crazy."

“ _No,_ ” Rory said emphatically, “he's not crazy at all. You’re amazing, Jess. I’m just glad they all see what I see."

 

**AGE TWENTY-THREE, JANUARY. PHILADELPHIA**

“Jess?” Rory called out into the quiet loft, slipping her jacket off her shoulders and onto their weird abstract coat hanger. “You home?”

“In the bedroom,” Jess called back and she found him half naked in their room wearing nothing but a pair of tight black briefs as he rummaged through his drawers for clothes. “What’s up?” He asked, looking at her over his shoulder. Rory could smell the masculine notes of his soap and inwardly swooned over the way his hair looked when freshly washed.

“I, uh…” she trailed off, eyes roaming all over his body, unsure of where exactly to look first.

He turned to look at her, eyebrows raised. “Enjoying the show?”

“No,” she said a little too harshly and he raised his brows higher. “I mean yes,” she corrected and one of his eyebrows stayed raised as another came down. “I mean... maybe? I don't know!” Was her final offer, her face hot and red.

Jess just laughed and turned back to the dresser, grabbing a clean pair of PJ pants and slipping them on. “Better?”

“Yes, thank you.”

“Okay, so, what do you need?”

“I actually wanted to talk to you about… _this_.”

“What?” He asked, grabbing a plain black shirt and throwing it over his head and covering up his torso.

“You.”

“Me?”

Rory nodded. “Yes. You. All of you," she said, feeling like she was about to start rambling any minute. She just needed to get this out, so she took a deep breath and began, "Listen, Jess, I get that you’re very comfortable in your own skin and I know I’ve never made it clear that I’m uncomfortable with you walking around in all your half-naked glory but I am. Uncomfortable, that is. I am uncomfortable.”

“Oh,” Jess said, looking a little taken aback. “I’m sorry. I didn’t know. I’ll, uh, definitely make it a point not to do that around you anymore. I’ll let Matt and Chris know, too—don’t worry.”

She chewed on the inside of her lip and wondered if it was worth it to admit that she didn’t _care_ about Matt and Chris walking around in their underwear because she wasn’t attracted to either of them like that. Honestly, she hated the way he approached everything with maturity now. Seventeen-year-old Jess had never been _this_ emotionally stable, willing to listen or downright accommodating, but now he was practically a saint.

“Actually,” Rory said before she could stop herself, wanting to be as honest as him. “It’s just you.”

“Just me?”

“Yeah,” she squeaked, looking down at her feet.

“Okay,” he said slowly and Rory couldn’t bring herself to look at him. “I feel like something’s happening here.”

“No, nothing’s happening,” Rory denied vehemently, looking up at him finally. “It’s just, you’re my best friend and you’re an attractive person… and sometimes when you walk around here with no clothes on I get… confused.”

“Confused?” Jess asked.

“Yes,” Rory said with a nod. “Confused.”

“Is confused a synonym for horny?”

“ _Jess!_ ”

He looked at her with wide, anticipating eyes. “I’m just trying to understand, okay?”

“This is such an awkward conversation,” Rory complained, regretting her decision to talk to him about this. She turned on her heel to stomp out of their room but he caught her before she could leave and twisted her to face him. “Please let go,” she begged, feeling as if she were about to suffocate from how close they were.

He let her go and stepped back but reached for her hand to keep him with her. “Just answer one question, okay?”

“Fine.”

“Are you sexually attracted to me?”

She closed her eyes and took in a deep breath, held it for a moment and then let it go. “Yes.”

“And you asking me to cover up was your way of doing something about it?”

Rory nodded, feeling too self-conscious to speak.

“Okay.” He let her hand go. “I understand.”

“You do?”

“Completely.”

She bit her lower lip. “Is this going to make things awkward?”

“No.”

She didn’t believe him. This just seemed too easy. “You don’t think it’s weird that I’m attracted to you?”

Jess shrugged, stepping further away from her. “Not at any more than me being attracted to you. I thought you knew that I was.”

“I…” she didn’t know what to say. “I guess I never thought about it. I was just distracted by my own feelings.”

“Well,” he said, voice airy and light, “I am. I think about it a lot, but we’re friends and I don’t want to cross any boundaries.”

“Plus, Avery’s back in your life now, too…” She was fishing, she knew she was fishing, and she knew that Jess knew she was fishing.

“We’re not back together or anything,” he humoured her. “I wouldn’t worry about it.”

“I wasn’t worried.”

He smirked at her, disbelieving. “Good.”

“Yeah, good,” she said, looking back down at her feet.

“You hungry?” Jess asked as if they hadn’t just been talking about wanting to fuck one another. “I can make us some dinner. Matt and Chris are out doing god knows what, so who knows when they’ll be back.”

Rory willed herself to look at him again, stuffing down the slight disappointment she felt knowing that their mutual attraction wasn’t going to take them over a line neither of them _really_ wanted to cross.

“I’m starving, actually.”


	3. Chapter 3

**Notes for the Chapter:**

> Avery's not quite out of the story yet, but we'll be wrapping her up soon probably! As always, don't forget to leave a comment because I love to know all your thoughts!
> 
> Also, sorry for any mistakes because I haven't edited this lmao.

**AGE EIGHTEEN, DECEMBER. STARS HOLLOW.**

Lorelai came home from work to find her daughter curled up in bed under a half a dozen blankets while sobbing her eyes out. She put her purse down on the kitchen chair and rushed into Rory’s room, calling to her softly in hopes of not startling her.

“Rory, honey… Is everything okay?”

“No,” Rory said thickly, barely audible from being buried underneath all those blankets.

Lorelai started to pull them all off of her, one by one until she struck gold. Her fingers made their way to Rory’s hair automatically, stroking the crown of her head. “What’s wrong, babe?”

“Everything!” Rory sniffed, voice still muffled as her face was shoved into a pillow. Her body wracked as she spoke and Lorelai could feel her broken breaths that shook the bed. “I hate Jess so much!”

She sighed, figuring that she should’ve known Jess would’ve been the problem. “What’d he do now?”

“He’s going to New York with Avery for his birthday!”

Lorelai slumped forward a bit in disbelief, grateful that her daughter couldn’t see the look of judgment her face. “That’s all?”

Her daughter flipped onto her back, wiping at her eyes with the heels of her hands. She gave her mother a furious glare, her mouth set into the deepest of frowns and her blue eyes still hazy with tears. “What do you mean that’s all?! Jess and I always spend his birthday together!”

“Well, yeah, but he’s got a girlfriend now…”

“So?! I have Dean and I still invited Jess to my party.”

“But Jess isn’t having a party, Rory… He’s going to New York. The big apple! His home city! Don’t you think that’s exciting for him?”

“I would go with him to New York,” Rory said indignantly.

Lorelai sighed and placed her hand on her daughter’s shoulder. “I know you would, honey. But Jess wants to go with Avery.“

“You do know this means Luke won’t be in town for Christmas because he’s going too.”

She shrugged. “So? Luke could use a little fun on the town, don’t you think?”

“Fine!” Rory snapped, laying back down in bed and twisting away from her mother. “I’m just a selfish bitch who doesn’t want Jess to go to New York without me then!”

“Hey, I have dibs on being the selfish bitch in this household,” she joked, rubbing her hand up and down Rory’s back. “Have you ever considered that maybe you’re _jealous_ of Avery, honey?” When Rory didn’t say anything, everything clicked. “Oh. You already _know_ you’re jealous of Avery. That’s why you’re so upset.”

“I don’t want to be jealous,” her daughter admitted miserably. “Avery’s nice. There’s literally nothing bad about her. Her parents grew up and met in New York at Columbia, they raised Avery there until she was three and they moved to Stars Hollow when her little sister was born. That’s so much more interesting than little ol’ Town Princess Rory. Avery’s artsy and really smart and Jess likes her and her family likes him and they’re having sex and I’m _jealous!_ ”

“Whoa,” Lorelai said, trying to process the last thing in her daughter’s rant. “Back up. You’re jealous that they’re having sex?”

Rory didn’t say anything again and Lorelai squeezed her eyes shut tight, trying her best not to judge.

“Okay… Babe, I think this is turning into a whole different conversation.”

“No, it’s not,” Rory said, turning to face her again. “You suggested that I’m jealous of Avery, and I’m telling you that I am.”

“Yes,” Lorelai said slowly, “but you see…. When I suggested that, I was suggesting that you’re jealous of Avery because she’s taking away your _best_ _friend_ … but you said you’re jealous because they’re having sex, which, suggests that you… maybe want to be the one having sex with Jess?” God, this was her worst nightmare come to fruition.

“No! God, no!” Rory denied, sitting up again. Her face was beet red in a way that betrayed her true feelings and Lorelai’s stomach sank. “I don’t want to have sex with Jess! I love Dean and I’m going to be with Dean forever!”

“Forever’s a pretty long time, babe… Not everyone marry’s their high school boyfriend—I sure didn’t.”

She liked Dean, a lot. He was kind, sweet and very helpful. He treated her daughter like royalty for the most part, and Lorelai knew that he’d probably die for Rory if it ever came down to it. Dean was the kind of boy a mother _wanted_ their daughter to date, but that didn’t mean that her daughter still wanted to date him. People fell out of love all the time, especially teenagers.

“Well, Dean and I will,” Rory said, though it sounded a lot like she was trying to convince herself. “We’re not like you and Dad.”

Lorelai didn’t have it in her to argue; she was tired from work and she didn’t want the idea of Jess in Rory’s head anymore than he already was. “Okay, hon. So, if that’s not the issue… What is?”

Rory bit her lip and looked down in her lap. “It’s just that… Jess is _technically_ younger than me by about two months and a half, and Avery’s younger than me by a whole _year_ and they’re having sex and I’m… I’m _not_. I’ve been with Dean for almost _three years_ and the thought of it has never even crossed my mind! What does that say about me?”

“That you’re the good kid?” Lorelai joked, but it felt like the truth to her.

“I’m not _the good kid_ because I’m not having sex,” Rory argued, sounding disgusted. “Lots of teenagers have sex, in a very safe way might I add. There’s nothing inherently wrong with being sexually active as a teenager. It’s natural.”

Lorelai rolled her eyes. “You’re talking to the queen of teenage sexual activity, Rory.”

Her daughter looked away, seemingly embarrassed.

“Are you.. Are you _ready_ to be having sex, Rory? Because if you _are_ we’ll get you an IUD and I’ll buy you a whole pack of condoms and you and Dean can totally have at it.”

“Ew, Mom!”

Lorelai grinned. “Too much?”

“Way,” Rory said, her nose scrunched up in disgust. “But… maybe getting an IUD wouldn’t be so bad?” She fidgeted and averted her gaze from her mother’s eye. “…Y’know, just in case?”

Lorelai swallowed hard against the lump in her throat. “Yeah, sure, babe. Whatever you want.”

 

**AGE TWENTY-THREE, MARCH. PHILADELPHIA.**

The bar was disgustingly loud tonight, and Rory could feel her agitation rising. She was sitting in her typical booth with Jess, Matt, Chris, Val, Avery, and Jenn but she wasn’t having a good time. Jess sat to her right and Val to her left, she was stuck near the middle of the booth feeling as if she desperately needed to pee but she didn’t want to ask everyone to slide out for her benefit. She was starting to feel slightly claustrophobic.

Jess leaned in close to her ear to whisper his concerns. “You okay?”

She hated feeling his breath on her neck, it made her mind wander. “I’m fine.”

“You don’t look fine.”

“Well, I am,” Rory snapped and Jess backed off with his palms up.

“Okay. Sorry.”

She didn’t want to focus on how much she hated him right now so she picked up her vodka cranberry and took a long sip, relishing in the burn of vodka. Typically she didn’t like her drinks this strong, but the alcohol was helping to improve her mood and keep her mind off of her general life frustrations.

Work had been awful this week. She’d been bumped off a story due to _taking too long_. Her perfectionist nature criticized and her personhood insulted. She’d locked herself in the bathroom and called Jess to rant only to hear Avery in the background and her blood ran cold and the tears started flowing and she’d hung up after stuttering multiple apologies about interrupting their alone time. Jess had called back immediately, but she didn’t pick up.

2008 had brought Avery Ramesh back into Jess’ life in a way that Rory never thought she’d have to deal with again. They weren’t together is what Jess kept saying, but Avery had visited Philly at least seven times since New Years and it was only the beginning of March. If anyone asked Rory, it certainly seemed like they were on the verge of rekindling their past relationship. Didn’t really help that Jenn, Chris, and Matt were all enamoured with Avery, too. In a way Rory felt as if she’d been replaced.

Replaced on assignment _and_ replaced in life. God, she may as well have been eighteen again.

“I’ll be right back,” Jess announced and Avery moved from the end of the booth to let him out and slid into his place.

“Hey there,” she greeted with a tipsy smile and Rory smiled back automatically.

“Hey yourself. You look like you’re having a good time.”

“Oh, I am,” Avery said, pulling her second mojito closer to her before taking a sip through her straw, her wine coloured lipstick was starting to fade a bit from the inside. “You, on the other hand, look sad. How come?”

Rory shook her head. “Just… work stuff.”

“And Jess stuff?” Avery asked bluntly.

“No,” Rory lied, unable to help it. “Jess and I are fine.”

Avery cocked her head to the side with a smile. “You both keep saying that but I don’t believe either one of you.”

Rory didn’t know how to respond to that without digging herself into a hole. She could lie, but what would be the point? She could tell the truth but that would certainly cause problems and what was she supposed to say if she were honest, anyway? That she and Jess had admitted to a mutual sexual attraction two months ago and it hadn’t gone anywhere and Rory was angry about it? _Hey, yeah, so I know you’re fucking Jess again, but I want to fuck him too_. No. That would be ridiculous.

“It’s none of my business anyway,” Avery said after a few moments. She took another few sips of her drink until it was done and pushed it away from her. “I hope you feel better soon though.”

“Thanks,” Rory mumbled.

Jess came back a few moments later with a platter of drinks. Avery moved to get up but he motioned for her to stay next to Rory and he took a seat at the end of the booth. “One mojito for Avery,” Rory heard him say just as Avery took her new drink. “One vodka cran for Rory.” Avery slid Rory’s drink to her with a smile and Rory felt her stomach flip; Jess hadn’t forgotten about her. “And a pitcher of beer for the rest of us.”

The rest of the night moved along rather well. Rory shook off her anger at the world and allowed the alcohol to make everything better, at least temporarily. She and Jess got into a fight about books, and various people chimed with something insightful to say. Jenn and Val giggled amongst themselves for the most part, and Matt and Chris locked their arms around each other’s shoulders and sang to the bar music at the top of their lungs until Jess told them to shut up.

Rory was having such a good time by the end of the night, that she didn’t even want to die when she caught Jess’ hand sneaking up Avery’s skirt. In fact, she found it kind of hot, and she let herself watch with a sort of inappropriate curiosity. When she looked up, Jess was watching her from Avery’s other side, eyebrows raised and smirk in place almost as if he were including her in the act. Rory blushed, choosing to look away at that moment but found herself glancing back down at Avery’s toned legs every so often, noting that Jess’ hand was completely under her black mini now.

It seemed like no one else was the wiser to Jess and Avery’s under the table action. They had great poker faces, Rory thought. Jess carried on a conversation with such ease as he touched his ex, and Avery fluttered her eyes shut sometimes and licked her lips in quiet satisfaction but otherwise kept her face impassive. Rory wondered why on earth she wasn’t feeling her typical disgust at their actions, surely sober Rory would’ve been revolted, but maybe alcohol really was the fix for everything.

“I need to pee!” Val announced and Jess slowly took his hand back from the apex of Avery’s thighs and Rory could see the glisten on his fingers. She exhaled hard and focused on keeping herself steady as she slid out of the booth for Val to get out. When she stood, she stumbled into Avery, reaching out to steady herself on the shorter girls shoulder.

“Sorry,” she whispered, wanting to say something more but she had no idea what.

Avery smiled up at her and gathered her curls up into a messy top knot, securing it with a pink elastic on her wrist. “No worries.”

“Rory,” Val said sweetly. “Come with me to the bathroom?”

And suddenly, Rory had never been more grateful for Valerie Marquez in her entire life.

“So, what’s the deal between Jess and that chick?” Val asked as they washed their hands.

Rory had almost forgotten how badly she’d needed to relieve herself and suddenly she felt a lot lighter, though she could feel her heart beat between her legs. She was doing her best to ignore that.

“Who? Avery?”

“Yeah.”

Rory moved away from the sink to grab some paper towel to blot her hands. “She was Jess’ high school girlfriend. They were together for three years.”

“And are they back together or…?” Valerie leaned into the mirror to get a better look at her reflection; she was a small girl, smaller than Avery by about half an inch Rory had noticed. Her hair was very long and pinned back from her face with a braided crown while the rest of it was tucked into a loose ponytail. She tugged it out of it’s hold and threw the elastic band into her purse before reapplying her lipstick and Rory wished she’d carried her purse with her too.

“Jess keeps saying they’re not.”

“But they’re definitely screwing.”

Rory sighed, throwing away the paper towel. “Seems like it,” she said, thinking back to Jess’ glistening fingers and the electric shock that ran down her spine. He hadn’t even been touching her and yet, in the end she was more aroused than she was jealous.

“Do you think she’s a good lay?” Val asked, her eyes never leaving her own reflection; she pursed her lips to spread the pink pigment around to her liking.

Rory choked on her own spit. “What?”

Val leaned away from the counter and turned to look at Rory, head cocked to the side. “I’ve slept with Jess before—a few times, actually. He’s very particular about what he likes in bed. I'm just wondering if she’s good at it.”

Rory blushed. “I don’t know? She’s probably had a lot of practice at whatever it is he likes…” She hated this. She hated every single thing about this conversation.

“I bet she’s a pro if he's choosing her over me.”

She wanted to ask what exactly Avery could be a pro _at,_ but she didn’t want to seem desperate for information on Jess’ sexual preferences. “I guess.”

“Well, whatever,” Val said moving past Rory and to the door with a wink. “Thanks for the information. See you back at the booth.”

 

**AGE EIGHTEEN, JANUARY. STARS HOLLOW.**

Once upon a time the winter carnival had been Rory’s favourite of Stars Hollow festivals, but now she wasn’t so sure.

The town square looked as beautiful as it always did, and in a lot of ways Taylor had really outdone himself this year. The twinkle lights were gorgeous against the backdrop of snow, and the array of booths looked just about as fun as they always did but somehow none of it seemed remotely appealing to her now. Maybe she was out growing Stars Hollow. Could that even possible? Did a person suddenly turn eighteen and start to lose their love for all the childish wonder in the world?

Dean talked a mile a minute beside her, but she was hardly listening. They’d decided to take his little sister, Clara, with them to the carnival this time and Rory was glad to have a buffer. Clara was a cute kid, a little annoying and bratty, but cute all the same. She loved her big brother so much that she hated sharing him with Rory, so in the end she wouldn’t have to talk to Dean much tonight.

At the age of sixteen all Rory had ever wanted was for Dean to pay her close attention, ignore everyone else and treat her like the only person in the world. And oddly enough, he had. He’d been doing that for three years now without letting up, but three years was a long time to bask in that sort of attention.

Dean was perfect, Mom said. He’d never done anything bad to her; he was kind and patient and didn’t force her into doing anything she didn’t want to. Two years of dating and the topic of sex had never even so much as come up between them, even after that breakdown she’d had in front of her mother last month. Mom liked that that there were no updates on the situation but Rory didn’t really know if it was a good thing. Dean was perfectly nice, but maybe that was the problem. Maybe he was _too_ nice.

Didn’t help that Rory didn’t know how to broach the topic of sex without bringing up her fight with Jess. Dean was insecure enough about their friendship without Rory making it any worse.

“Hey, Rory. You want me to win you one of those bears?” Dean was pointing off to one of the booths.

She nodded along dumbly, still a little distracted by her own thoughts.“Yeah, sure. That sounds nice.”

If he’d noticed that she was distracted he didn’t let her know.

There were a few people already at the booth, a small crowd gathered in a semi-circle as they watched someone take a crack at the game. Rory pushed up on her toes to see what was happening, but there was a particularly tall man in front of her that ruined the view. Finally, the group seemed to disperse and Jess and Avery came into view just as Jess handed his girlfriend a small bear with a kiss that made Rory’s face burn. She scuffed her boot against the snow and averted her eyes.

“Rory, Dean. Hello,” Avery said a little breathlessly, now free from Jess’ liplock, though his arm was still wound tight around her waist.

Rory forced a smile and Dean gave a genuine one. “Hey,” the couple greeted at the same time. Rory tried to catch Jess’ eye, but he avoided her gaze.

“I’m going to go grab some hot chocolate,” Jess said to Avery. “You want any?”

“Yes, please.”

He kissed her cheek in affirmation and set off without so much as giving Rory a glance.

Rory fiddled on the spot, interlacing her gloved fingers and swaying awkwardly as she, Dean and Clara were left alone with Avery. She was sure it wasn’t awkward for anyone else, especially as Dean and Avery managed to strike up a conversation quite easily, but she felt out of place.

“I want hot chocolate, too,” Clara interrupted, looking up at her brother in bratty demand.

Dean laughed. “Sorry to cut this short,” he said to Avery but she just told him not to worry about it.

“It’s okay, Dean,” Rory piped up, finding this the perfect excuse to leave. “I can get it. You two keep on talking.”

“You sure?”

“Completely,” Rory said firmly, leaning up to kiss him softly. “Stay right here, I’ll be back soon!”

She set off for the hot chocolate booth, finding Jess waiting in line with his hands stuffed in his pocket. She bit her lip on as she approached him, boots crunching in the frozen snow.

“Hi,” she said awkwardly once she reached his side.

He glanced at her for what felt like forever before looking away. “Hi.”

“Just here to get some hot chocolate for Clara and Dean. Maybe for myself, too. But I’ve always been more of a coffee girl, not that you don’t know that. Sorry, I’m rambling. I just, yeah… Here for Clara.”

“Huh.”

“I didn’t think you’d be here—at the festival I mean. Not in line, I knew you’d be in line because you said you were coming over here. I just mean… you’ve never really cared about these town things before.”

Jess shrugged. “Avery wanted to come, so I came.”

“Oh.” She looked away from Jess, glancing around at anything and everything that wasn’t him, suddenly feeling nervous. Her fingers felt hot and slimy inside of her gloves. “Jess…” Silence. Deep breath; inhale, exhale. “Are you still mad at me?”

He took a while to answer, maybe a beat or two. “I don’t know. Should I be?”

“Well, we haven’t really talked since your birthday…”

“Not my choice,” Jess said smoothly, his eyes focused on nothing the line ahead of them. “I never told you to keep your distance.”

Rory sighed, peeling off her gloves to alleviate some of the discomfort in her hands. The crisp January air felt good on her skin. “I know, I just don’t like fighting with you, and whenever we fight I avoid you because it’s hard to see you and not be able to tell you about what book I’m reading or a bad movie I watched with my mom, plans I have with Lane or how crazy Paris is…”

He didn’t say anything and Rory felt as if she was going to vomit.

“Don’t… you feel that way too?” She asked timidly.

Finally, Jess turned to look at her and Rory’s breath hitched in her throat. He looked so handsome against the backdrop of the carnival with his wavy pompadour and olive skin. She hated that she felt this way.

“Of course I do.”

“So… Truce?”

She watched him take a deep breath, leather jacket expanding as he inhaled long and deep. When he let it go, his shoulders seemed to relax and the guard he’d had up just a few seconds ago seemed to drop.

“You said some really awful things, Rory.”

“I know.” She looked down in shame, feeling hot from the inside out. “I’m sorry. I shouldn’t have been so judgmental about you and Luke going to New York with Avery and her family for Christmas. I just… got a little jealous, I guess.”

“A little?” He asked incredulously, staring at her with a crinkled brow and a frown.

“A lot,” she corrected, shifting uncomfortably as they moved up pretty far in line.

“Rory…” He started, sounding a little sad but also exasperated. “She’s my _girlfriend._ ”

Rory nodded, blinking away the stupid tears threatening to surface from behind her eyes. “I know.”

“And _you_ have a boyfriend.” She swallowed thickly, nodding. She knew that too, of course, but Jess had every right to call her out.“So, you can’t get mad at me when I don’t choose you every single time because you certainly don’t choose me every time.”

“You’re right. I’m sorry,” she choked out, feeling like she was going to vomit if she had to say anymore.

He nodded. “For what it’s worth, I’m sorry for my part, too. I didn’t mean to make you cry or ruin your Christmas, if I did.”

“Thank you.” Rory didn’t feel like she deserved an apology out of him; she was the one who’d messed up.

“So, truce?” He repeated her earlier question and Rory smiled just as they made it to the front of the line.

She looked at him, feeling elated. “Truce.”

 

**AGE TWENTY-THREE, MARCH. PHILADELPHIA.**

Rory stared at the clock on her nightstand and listened to the sound of Jess’ breathing. He wasn’t snoring, so that meant he had to be awake. It was almost two in the morning and they’d just got home from the bar about a half hour ago. Matt hadn’t even had the wits to pull out his bed from the couch and chose to pass out on top of the cushions. Chris walked Val and Jenn home like the gentle man he was and came in such a few moments after them, and Jess hailed Avery a cab and kissed her goodnight in front of everyone.

She was still kind of tripped up by her own reaction to watching Jess pleasure Avery in public; she’d seen them do something similar on New Years, but she hadn’t been all that drunk that night, unlike tonight. Rory sighed and flipped onto her back, pulling her own personal blanket up a little tighter to her chest.

“Jess?” she said into the darkness and she felt him move beside her.

“Mm?”

“Do you and Avery have sex in public a lot?”

She heard him inhale, but didn’t hear him exhale though she felt it as his arm pressed against hers. “Not a lot, no. Sometimes though.” The fact that she’d asked and he answered meant they were definitely still drunk. “I’m sorry I did that in front of you. It was crude.”

“I actually kind of liked it,” Rory admitted, so glad he couldn’t see her face.

His breath hitched and she felt proud of herself. “Yeah?”

“Yeah. I felt… included. Like you were putting on a show for me.” She grinned up at the ceiling, twisting in her blankets to face him with a new found courage. “I want you to do that to me.”

“Touch you in public?”

“Touch me in general.”

He laughed, soft and quiet and she heard the rustle of his blankets just before the cool air hit her legs but they were quickly warmed up by Jess’ own. She shifted to intertwine their legs together, grinding herself down on his knee with a small groan as she latched her arm around his shoulders. His hands traveled the length of her thigh starting at the back of her knee and stopping at her hip as he firmly grabbed at her flesh.

“I thought we agreed not to do this,” Jess whispered into her hair but Rory just pushed herself closer to him, desperate for release.

“Technically, I never agreed to anything.”

She kept a steady rhythm in her grind against his leg, picking up in speed when she could feel the pressure building. Her breathing was laboured and broken as she panted wet and hot against his neck and his hands trailed up her camisole to touch her breasts, kneading them and tugging at her nipples. They didn’t kiss, though Rory sucked on his neck to keep herself quiet as she came, her teeth nipping at his skin as she jerked against him three times in climax. She breathed hard and fast as she came down but she pushed herself up and forced him down so she could straddle him.

The length of him was pressed hard into her center. She rocked back and forth slowly along him and he let out a long, torturous groan, his finger tips digging into her hips. Rory dragged her nails down his shirt until she reached the hem and pulled it out from under her thighs and pushed it all the up.

“Take it off.”

He sat up, did as his was told and once he was bare chest Rory forced him back down. “Wow, you’re assertive in bed.”

She leaned down and kissed him then, cupping his face in her hands to take control. Their kiss was nothing like their earlier actions. It was sweet, almost innocent and Rory wondered if he’d ever kissed Avery like this. She pulled back to stare into his eyes and let a goofy smile take over her whole face.

“This is happening,” she whispered, leaning down to kiss him again but there was a hesitance in his kiss this time that made Rory’s heart skip a beat.

Jess leaned back into the pillows to break the kiss. “Wait, no,” he said stirring beneath her. “What do you mean this is happening?” He kept struggling to get free. “ _This_ can’t happen.”

“Jess—“

“Rory, we said we weren’t going to cross this line.”

“But I want to.”

“You’re drunk.”

“So are you!”

“Even more reason for this not to happen!” He hissed.

Rory kept her position on his lap, but stilled her rocking. “Are you serious? You don’t want to do this?”

“Of course I _want_ to do this,” he reaffirmed how much by flexing his hips up into her so that his erection pressed against against her. She fought off a moan, not wanting to give him the satisfaction. “I just don’t want it to be _like this._ ”

“Because Avery, right?”

“She has nothing to do with this, Rory! I’m not _with_ her. We aren’t monogamous. How many times do I have to say that?!”

She rolled off of him, taking her blankets with her and leaving him bare. “Fine. You just don’t want to be with me because you don’t. I got it. Goodnight.”

“Rory, don’t be like that.”

She closed her eyes, trying to get comfortable on her pillow.

“Rory…”

“What?” She snapped, glaring back at him.

“I’m sorry.”

“Whatever.”

He sighed and she heard him get off the bed. “I’m going to sleep on the floor, okay?”

“You do that.”

 

**AGE EIGHTEEN, MAY. HARTFORD.**

“You’re not going to prom?”

“Nope.” Jess shelved the last of the books from the new inventory; maybe Andrew would let him leave early today. “Prom is stupid.”

Rory gasped in offense. “Prom is wonderful and magical! I’ve been dreaming of Stars Hollow Prom for, forever!”

“You don’t even go to Stars Hollow High,” he retorted drily.

“So? Dean does and I’ll be his date. Plus, Lane will be there and she’s going with Dave and I just thought that you’d go with Avery and we could all have fun together!”

Jess rolled his eyes and pushed past her, wheeling the inventory cart back it’s place at the back of the store. “Sorry to disappoint. I just think it’s lame.”

“What’s so lame about it?” Rory asked, blue eyes hardened with the determination to undermine any argument he had.

“You dress up in a fancy suit and a dress, rent a limo and go to a fancy dinner with a bunch of people you probably don’t even like. The dance floor is hot and sticky and everyone smells from the mix of B.O, perfume, cologne and those stupid flowers on your wrist or in your breast pocket. If you went with someone you like then maybe you rent a room at a hotel somewhere and lose your virginity like a fuckin’ sheep.”

When he finished his rant he looked back to find Rory glaring at him. “Well, yes, I agree that prom sex _is_ stupid, but everything else doesn’t sound so bad. It could even be fun. Great memories and all.”

“To each their own.”

Rory pouted at him as she followed him to the cash register, waving around a thick book as she raved at him, “It’ll be fun, Jess! Come on! Since you moved here I’ve dreamt about you being at prom with Lane and I, and it’s perfect because no one will be a third wheel. You have a girlfriend, I have a boyfriend and Lane has a boyfriend! No one will be left out.”

“Rory, I’m not going to prom. Now, are you going to buy that or not?”

She looked down at the old, worn book in her hands and blushed before dropping it onto the counter. “Yes, please. Can I borrow your employee discount too, maybe?”

He grabbed it and scanned it, typing in a code on the cash register and showed her the price of fifteen dollars.

“Wow, that’s a good deal!” She said, forking over a twenty and he handed her back a five. “I love your employee discount. Thank you so much, Jess.”

Jess smirked at her, placing the book into a bag before handing it off to her and leaning against the counter. “You read the Sun Also Rises again yet?”

She scrunched up her nose. “No. You know I haven’t.”

“I know, I just like to tease you.”

She blushed for some reason, and Jess laughed under his breath. “Anyway,” Rory said, blinking rapidly. “Avery doesn’t want to go to prom, either?”

He sighed, tipping his head back with a loud groan. “Seriously? We’re back on the topic of prom?”

“I just think it’s weird that Avery wouldn’t want to go!”

“It’s not _weird_. Avery’s just not really into that stuff.”

Rory nodded, looking self-conscious. “I guess that’s why you like her.”

“There are other reasons.” He knew that Rory was writing a compare and contrast essay between herself and Avery right now, just as she seemed to do almost every day. “If I had a girlfriend who liked that stuff, I would go for her. Avery’s just not that type of girl.”

“Right.”

“You’ll have fun without me.”

“I’d have more _with_ you.”

Jess shook his head. “You’ll be so focused on Dean that you won’t even notice I’m not there.”

“That’s not true,” Rory murmured. “I always notice when you’re not there.”

He smiled a real smile. “That’s cute. But seriously, it’s not a big deal, you and Lane do stuff without me all the time. Just be sure to give me all the details and take lots of pictures. I might even show up to the after party the next day.”

Her eyes lit up then and she smiled, bouncing on the balls of her feet. “Really?”

“ _Maybe._ ”

 

**AGE TWENTY-THREE, MARCH. PHILADELPHIA.**

Jess didn’t know why he came here. He could’ve went anywhere—a bar, Truncheon, a cafe—but instead he’d wound up at Avery’s hotel room on her bed watching TV as she ordered them room service. There was nothing good on, and he firmly believed that television could rot your mind no matter how much he loved _I Dream of Genie_. Didn’t help that he thought television was getting worse. There were hardly any shows on that he really enjoyed, so he settled for the stupidest sitcom he could find.

“Yep. Yep, that’s correct. Oh, no, that’s okay I think we’re good. Yeah, you too. Thank you so much!” Avery said into the phone before hanging up and joining him on the head. She laid her head on his shoulder and he absentmindedly ran his fingers through her soft curls. “You going to tell me what’s wrong yet?”

“No.”

He felt the curve of her smile. “Figures.”

They sat in silence, watching some old episode of Two and a Half Men until a swift knock came at the door. Avery hopped off the bed to grab the food from a hotel assistant, thanking her profusely. Her and Jess ate their burgers and fries without talking and Avery put the cart out in the hallway once they were done.

“You going to tell me what’s wrong _now?_ ”

Jess sighed, gesturing her over to the bed. She rested against him with her leg thrown haphazardly over one of his. “It’s Rory.”

“Duh.”

He smirked down at her and held onto her a little tighter. “We almost had sex last night.”

Avery froze against him for a beat before relaxing again. “Oh.”

“Does that bother you?”

“Do you want it to?”

Jess shrugged with a laugh too thin and wheezy to survive. “I don’t know.”

“Jess, I meant what I said on New Year’s. I’m not here looking for a ring or some sort of big commitment.”

“I know.”

“I get that we always said that maybe after I graduated college we’d reconnect, but I think we were just saying stupid kid shit… I didn’t think it’d happen.”

“Huh.”

“Did you?”

“Maybe. I don’t know. Part of me hoped for it, I guess.”

Avery took a deep breath and he felt the need to mimic it. She twisted in his arms to look up at him. “I live in Boston.”

“I know.”

“And I actually _like_ Boston.”

“I know.”

She nodded, seeming satisfied before twisting back into her regular position and leaning back onto his chest and arm. “So. You and Rory, huh?”

“Me and Rory.”

Avery laughed then, melodic and sweet. “I fucking knew it.”

Jess laughed too, unable to help fight the infection of her own. He grabbed her and rolled on top as he balanced himself on his hands above her. “Shut up.”

“You should tell her how you feel.”

“No, I shouldn’t.”

Avery studied him with serious eyes. There was something about her that always struck him as being soulful and wise. Maybe that had been what attracted him to her in the first place. “If you love her you should.”

“I don’t know if I love her.”

“Yes you do,” she whispered. "You do know."

He groaned, pushing himself off of her and onto his back. He brought her in close and kissed the top of her head. “She’s not as clear cut as you are in my mind.”

“That doesn’t mean your feelings aren’t real.”

“I hate you,” Jess chuckled. “You make me feel stupid.”

“You’re not stupid, I’m just more emotionally intelligent than you are. Rory, too. That girl is dumb as bricks emotionally.”

Jess smirked. “You should’ve seen her with Huntzberger”

“Not sure I could’ve handle that if it was really as bad as you're implying.”

“I just…" Jess said, getting back on topic. "It’s not that I’m not attracted to her. I am. I have been since I was sixteen, but everyone—her mom, Luke, her dad, her grandparents, Taylor, Babette, Miss Patty, and lord knows who else _all_ made it very clear that I was not good enough for her. And… I internalized that. I’m twenty-three and I look at her and I _still_ am terrified of crossing the point of no return.”

“You’re not sixteen anymore and Rory’s no longer the Town Princess. If you want to be with her, you should be.”

“Realistically I know that, but I don’t feel that way… I mean, yeah, I want to be with her but she’s not just _Rory_. She's  _the_ Rory, precious jewel of practically everyone.”

“You’re not in Stars Hollow, Jess. You could be together without the town judging you.”

Jess shook his head. “No, Rory’s not that type. If I’m with her, it’s gotta be the whole package—the mother, the grandmother, the cooky town. And they all hate me, and honestly? I’m not all that fond of them either. I’m accomplished, I run a business, I’ve published a book and I, apparently, got her to go back to Yale and yet I’m still not good enough. I’ll never _be_ good enough for Rory Gilmore.”

Avery hummed. “Those people really fucked with your self-esteem, huh?”

“I don’t think I would’ve graduated or been half as stable as I am today if it weren’t for you.”

“I don’t believe that. You would’ve figured it out on your own.”

He snorted. “Yeah, while on my death bed or something.”

“Don’t be self-deprecating,” She reprimanded, “it’s not cute. Despite what you say, you are extremely resilient, Jess. You would’ve wound up exactly where you were meant to because you’d have made sure of it.”

“You think quite highly of me.”

“I do.”

He shifted to bring her in, not that she could get any closer. “This isn’t just sex for me,” he said, somehow overcome with the need to explain the way he felt about her. “I’m not just using you to get off. I don't want you to think that because of my complicated situation with Rory that you're just some girl o me.”

Avery shrugged. “ That’s good to know. I’m not using you, either. You're too important to me to fuck with that way.”

“You see? That’s why I can’t be with Rory. She just… I just have this feeling that all she wants sex right now, and then we’ll do it and it’ll ruin everything.”

“Would you be crushed?”

He didn’t quite know the answer to that. “Sometimes I think I would be, and other times I’m not sure. You know that whole idea of toeing the line between friends and lovers?”

“Mhm.”

“I feel like Rory and I are more so toeing the line between friends and lust, and I think that’s a worse line to cross.”

 

**AGE EIGHTEEN, JUNE—PROM NIGHT. STARS HOLLOW.**

Rory couldn’t get Jess’ words about prom out of her head as she looked around at the elegant hotel room Dean had booked for them. She hadn’t even considered the idea of having sex on prom, she just knew that it was a stupid thing that a lot of people did and, as such it was something she’d never wanted to do. But, now she was here, standing in this room and there were rose petals on the bed and sparkling, non-alcoholic peach wine and Rory could feel her resolve slipping away. He had went through all this trouble for her. Wouldn’t it be rude to say no?

Dean was holding her hand, looking down at her expectantly and when she didn’t say anything for a while shook her lightly and gave her a nervous grin. “So? What do you think?” He asked, looking around.

“It’s… nice,” Rory said, unable to think of any other words. “Very uh… nice.”

“Nice? That’s it? Not romantic? Or elegant or beautiful? Just nice? Rory, I went through a lot of trouble to get us this room. I even embarrassed myself by talking to your mom about it to make sure she was okay with this!”

Rory snatched her hand away from him, rounding on him with her chin held high. “You talked to my _mom_?”

“Well, yeah,” Dean said, shifting uncomfortably under her gaze. “I know how close you two are, and when I said I wanted to keep you out a whole twenty-four hours she kind of put two and two together, and helped me find a really nice hotel near the prom venue. She got us a discount.”

“Oh my _god.”_ She suddenly felt sick to her stomach.

“Rory, come on… I mean, you got an IUD months ago right? And I have condom’s just in case. I thought you wanted this.”

“But sex on prom night is such a cliche!”

Dean rolled his eyes. “Let me guess... Jess said that, right?”

“Well, yeah… he did, once. But I agreed with it long before he said it.”

“Rory, you can’t let him ruin everything for you.”

“ _What?_ ” Her chest constricted and suddenly she felt like she couldn’t breathe. “Is that what you think of him? That he ruins everything for me? He’s my _best friend_ , Dean, and you talking badly about him is just like you talking badly about Lane!”

Dean moved closer and laced their fingers together, stroking the back of her hand with his thumb. “Okay, okay, okay. I’m sorry… it’s just, the guy really gets under my skin.”

“You should try to be nicer to him...”

“I just hate the way you seem to agree with him on everything. Before he came to town you just seemed so different.”

“I did not,” Rory said, wanting to snatch her hand away again. “I have a mind of my own, it just happens to be very similar to Jess’. Great minds think alike and all that jazz.”

"Okay, I'm sorry. You're right, but I  _really_ don’t want to talk about Jess anymore,” Dean said, pulling her in so close and fast that she practically lost her breath. “I really don’t want to _talk_ at all… If it’s that big of a deal to you then just pretend like it’s not prom night… Think of it as like, my _birthday_ or something.”

He kept his hold on her as he kissed her, backing her up slowly toward the bed. Her heart hammered in her chest as she hit the mattress and Dean climbed on top of her. They’d never really been horizontal before, and Rory wasn’t certain how to feel about it but Dean didn’t give her the time to think before he kissed her again and ran his hands along the silky blue material of her prom dress.

“You are _so_ beautiful,” he whispered before kissing her neck.

Rory finally let herself give in as she grabbed him by the collar to kiss him again and worked on removing the layers of his tux.

* * *

 

She didn’t know what sex was _really_ supposed to be like considering her only references had been novels, pop culture, and her mother--none of which accurately prepared her for the real deal. Rory really didn’t know if it had been good or bad. Dean had been well prepared, which was nice. There was no real foreplay, not that Rory really knew what to do anyways, but Dean had brought lubrication with him because he’d read on the Internet that it would hurt less for her that way. Rory never had the chance to ask where he got it from. When he slipped into her, it was a very odd sensation. It didn’t hurt at all, it was mostly just uncomfortable but it got better once she adjusted and he started to move.

There were no fireworks or seeing heaven or anything like that, and although it’d felt good for a time, Rory wasn’t exactly sure why it was that people thought sex was so damn fun. She laid there awake after they’d finished. Dean disposed of the condom and fell asleep soon after, but Rory felt an unsatisfied burning in between her legs. She’d orgasmed once before on her own when she’d been curious about her own sexuality and it’d felt infinitely better than what she’d just experienced, but she didn’t know what to do about it.

Dean snored lightly beside her and she sighed as she made her way into the bathroom.

She didn’t look any different, and she didn’t really _feel_ any different, but there was a sort of emptiness that she hadn’t been carrying around with her before. Rory shook her hair out from her up-do and stepped into shower, letting the hot water beat onto her scalp and run all down her body. Maybe she could wash the emptiness away. She scrubbed her face with her hands and soaped herself up with whatever little travel sized body wash the hotel provided, not even realizing that she was sobbing until she gasped for air and shuddered.

 

**AGE TWENTY-THREE, MARCH. PHILADELPHIA.**

Rory spun around in her chair at work, trying to clear her mind. Jess had avoided her all weekend, choosing to spend Saturday and Sunday out of the house. Chris and Matt had picked up on the tension between them, but neither of them said a word to her about it. She’d cried a little on Saturday after Jess packed a bag and left, but she hadn’t let it ruin her weekend. The memories she had from Friday night were a bit hazy, but she’d remembered what had happened in bed.

She groaned, leaning her head back against her chair. Had she always been this selfish? The more self-aware part of herself said yes, but the cute fifteen-year-old Rory that lived on in her heart said no.

There was a knock at her door just before Rory turned to face Avery. Her face burned with shame.

“Hi,” Rory said, sitting upright in her chair. “Did I know you were coming by?”

Avery shook her head. “No. I’m dropping by completely unannounced, sorry about that.”

“It’s fine.” She gestured to one of the chairs along the back wall. “Come. Sit.”

“Oh, no, it’s okay. I can’t stay long, I have a flight to catch in a few hours.”

Rory gave her a wry smile. “Leaving so soon?”

“Duty calls,” Avery joked, but it fell flat. “Jess should finally be home when you’re finished up here.”

“Ah,” Rory said with a sigh. “So, he was with you this weekend after all.”

“He was… And he was also a little upset which is kind of why I’m here.”

“Wow, he got himself his very own knight.”

Avery didn’t so much as smile at the joke attempt. “Rory, I don’t mean to be blunt but have you ever considered that all of this stuff between the two of you is really hard on Jess?”

“ _Of_ _course_ I have.” She didn’t mean to be so defensive, but it felt like her back was to the wall. Part of her wanted to ask what it was that Jess had told her, but she couldn't bring herself to ask.

“I think you’re great, Rory. You’re an intelligent, talented bibliophile who can keep up with Jess on his best day but… in some ways you’re kind of his greatest weakness.”

Rory furrowed her brow together, nostril’s flaring as she said, “And what about _you_ and all the things you’ve done?” She didn’t know why she was so angry. Maybe it was because she knew Avery was right, but the easiest thing to do was deflect.

“What have I done, exactly?” Avery asked, blinking in confusion. “Jess and I broke up amicably when I went off to college. There’s not much else to talk about.”

“Yeah, and that _wrecked_ him,” Rory almost shrieked but she was aware enough to keep her voice low in her place of work. “He was in love with you, did you know that?”

“I did.”

“And what? You don’t care? You just show up here after four years like ‘ _Hey, I’m back! Lets have sex!’_?”

Avery sighed, tucking a chunk of curls behind her ear. “You seem to be under this impression that I wasn’t devastated about the breakup, too. He was my boyfriend of three years, of course I was wrecked…”

“So, is that why you’re back? Because you still love him?”

“Oh, Rory,” Avery said both sadly and tiredly. “I’ll always love Jess, but it’s not like we’re gunning to spend the rest of our lives together.”

“So then why do you keep coming here?”

“Because Jess asks me to,” Avery said with an easy shrug. “He wants to see me, so I come and see him when I can. Anyway, I’m not here to talk about me or my relationship with Jess, past or present. I just wanted you to know that Jess is struggling emotionally right now and neither of us need to make it any more difficult on him.

“You love Jess, I know. He’s your best friend and there’s something else between you as well. Whatever is going on there is completely none of my business, but when Jess comes to my hotel upset and won’t leave the room for two days it starts to become my business. We’re not in high school anymore. I’m not, and was never, threatened by you and you shouldn’t be threatened by me.”

“Always the mature one,” Rory mumbled under her breath.

Avery came a little closer to the desk. “If you want to be with him then just do something about it. But please don’t just use him for sex, I don’t think he could handle that.”

“Why do you care?” It felt like her head was swimming.

“Because I care about Jess and he cares about you. He loves you, he just doesn’t feel good enough.”

“… Why wouldn’t he feel good enough?” She felt idiotic.

“You’ve never made him feel good enough.”

 _“Ouch,”_ Rory whispered to herself more than anyone.

“It’s not my intention to be mean, Rory. I just want to be forthcoming. Everyone back at home told Jess he wasn’t good enough for you, not platonically and certainly not romantically. His own uncle made it a point to sit him down and tell him how precious and special you are and how he’d break you and ruin you forever. Jess won’t risk hurting you and losing everyone he cares about. You’re a big risk for him to take, and he won’t unless he’s sure it’s going to work.”

Rory scraped at the skin of her lip and chose not to say anything.

“Just… try to go a little easier on him, okay? He’s kind of fragile.” Avery looked down at her watch and gave Rory a small, polite smile. “I should get going now… Maybe I’ll see you soon.”

“Yeah, maybe.”


	4. Chapter 4

**Notes for the Chapter:**

> Hello again! Welcome to chapter four where some things actually get resolved for literati in present day and worse for them in flashbacks hahaha. As always, don't forgot to leave me a comment and tell me all of your thoughts! I love feedback and talking to you guys!

**AGE EIGHTEEN, MAY. STARS HOLLOW**

“Your _Dad_ showed up?” Avery asked, squeezing Jess’ hand in support. “Just out of the blue like that?”

He shrugged a little. “Yeah.”

“Wow. How are you feeling?”

“Confused. Angry.”

“Did he say anything of use?”

Jess shook his head. “Not really.”

“Did Luke?”

“We fought about him. Luke knew he was here and didn’t tell me. Said he was trying to protect me but,” he kept his eyes on the floor. “I don’t know.”

Avery squeezed his hand a little tighter. “Do you want to get to know him? Your dad, I mean.”

“I don’t know.”

“It’s okay if you do, Jess. It’s completely normal, really.”

“Yeah?”

She nodded, moving in close to lay her head on his shoulder. “Yeah.”

 

**AGE TWENTY-THREE, APRIL. PHILADEPHIA**

Truncheon was busier than usual today. Jess only had an hour to himself for lunch before being thrust back into the swing of work. There was no downtime between arguing with the printers, assisting customers, and meeting with two of his writers to discuss the line editing and marketing of their novels. The only conversations he had with Matt and Chris were short, sweet, and work related, which Jess actually didn’t mind. His business partners and roommates had both been getting on his nerves in the past month.

They badgered him constantly about Avery and if they weren’t badgering him about Avery then they were badgering him about Rory. Jess just didn’t have the time or the patience to deal with it. He hadn’t seen Avery since her visit last month, and Chris claimed it was making him cranky. Jess didn’t know how to describe his relationship with his ex, if he could even really call her that anymore. The distinct lack of a label was slightly distressing, even if it had kind of been his idea.

“God!” Matt cried as he flipped the ‘open’ sign on the main door to ‘closed’. “Today was downright _exhausting,_ am I right?”

Jess hummed in agreement but busied himself with a stack of books, not really wanting to talk. Unfortunately, Matt did not take the hint.

“What do you think Rory wants for dinner?”

“Call her and find out,” Jess said curtly, but that still didn’t stave him off.

“ _Oooooor_ ,” Matt sang and Jess knew there was a sloppy, meddling grin on his face without even looking at him. “You could call her.”

Jess rolled his eyes. “Why me?”

“You’re her best friend.”

“I’m not the one wondering what she wants for dinner,” Jess said with a pointed look. “Stop meddling.”

“Who me?” Matt asked innocently. “I would _never_ meddle. Besides, what is there to meddle in? Things with the two of you are fine, right?”

“Yes.”

“Soooooo, you’re not fighting…?”

“No.”

“Okay, so, see! There’s absolutely nothing for me to meddle _in.”_

Chris came down from the apartment upstairs. “Okay, everything’s all set up for tonight.”

“Oh, goody.”

Jess turned to look between them, curious as to what Chris was referring to. “What’s set up for tonight? Did I forget something important?” He asked, noting the way Matt averted his gaze and Chris turned to glare at him.

“You didn’t tell him,” Chris accused and Matt shrugged a little. “Matt, what the hell were doing then?!”

“Hey! I was closing up shop and _trying_ to ease Jess into all of this but then you came down too early!”

“I gave you fifteen minutes,” Chris cried.

Jess cleared his throat, arms crossed tightly over his chest as he stared the two of them down. “Ease me into what?”

“Ease you into the fact that Matt and I are going to sleep here tonight.”

“What?” Jess asked, confused. “The apartment up there is falling apart… that’s why we rented the loft in the first place. _Why_ do you two need to stay here? Why would you _want_ to?”

Chris sighed, shifting from foot to foot. “Come on, man… You and Rory need the apartment to yourselves tonight to talk your shit out, properly. We’re all tired of you guys getting drunk, flirting, almost fucking and then acting like nothing happened the next day or just straight up _avoiding_ one another.”

“Rory and I have _nothing_ to talk about,” Jess argued, trying to keep calm. Anger was creeping its way up his back and his head was feeling light in agitation. “We’re completely fine! I don’t get what the big deal is. We’ve had a few drunken mishaps and if we act like nothings wrong the next day it’s because _nothing_ is wrong the next day.”

“Okay, well, even _if_ that’s true, which you _know_ it’s not, it still might be nice for you two to have the place to yourselves, maybe sleep apart. You can sleep in my room, or Rory can sleep in my room. Whatever you guys want. I know it gets cramped in the loft sometimes, there’s four of us in a two bedroom place, and it’s not like we can kick Rory out—“

“Not that we’d want to!” Matt interjected and Jess glared at him.

Chris nodded. “Yeah, no. We love her, you know that. It’s easier if we leave and then you guys can stretch out a bit.”

Jess pinched the bridge of his nose and closed his eyes tight. “You know this isn’t necessary right?”

“Yeah, it is. Jess, you _know_ it is.”

He opened his eyes to look at them and what he saw made him take a deep breath and reconsider what they were saying.

Yes, the living situation had gotten a little tense in the new year, but he didn’t think it was _that_ bad. Things with Rory had fallen back into their regular pattern by now; they didn’t talk about that one night last month, they didn’t talk about their attraction to one another, and they certainly didn’t talk about their love lives, but there was definitely still some tension. He’d caught Rory listening in on a conversation he’d been having with Avery on the phone, but he hadn’t called her out on it and she’d never brought it up to him. There was a part of him that wished she would just asked him whatever it was that she wanted to know, but he knew he’d probably have no answer to the question.

But, maybe the guys were right. Maybe he should take advantage of the empty loft, sit down and talk to her face to face about all their issues. It would be the adult thing to do, but that didn’t mean he was looking forward to it.

“Okay,” he conceded. “I’ll talk to her tonight. Thanks for doing this, I guess.”

“Be sure to tell us how it goes,” Matt said, sounding a little too excited. “You and Rory could fill up an entire gossip magazine.”

Jess snorted. “You don’t even know the half of it.”

 

**AGE EIGHTEEN, JUNE. STARS HOLLOW**

“Congratulations!” Rory shouted, mauling Jess with an extremely tight hug. She moved back to study him in his graduation gown and Jess tried not to make fun of her for it. She grinned up at him, innocent and fresh. “I knew you could do it!”

“Yeah, yeah,” he said, forcing a sort of nonchalance in his tone. He was excited to be done with high school, but he wasn’t about to let Rory know in fear of her never letting him live it down. “Thanks.”

Her smile never wavered and suddenly she was hugging him again before she planted a firm, lingering kiss on his cheek near the corner of his mouth. She blushed when he blinked down at her, smirk in place. “I should go find Dean and Lane,” she said in a rush, looking anywhere but his eyes.

“Okay, beat it,” he said, jerking his head off to the side.

Rory fiddled with the camera in her hand and looked up at him bashfully. “We’ll take a photo together later, right? Just you and me?”

“If that’s what you want.”

She nodded vigorously. “I do. I want one to match the one from my graduation. My mom and I got the idea to frame them side by side. I think it’ll look nice.”

He didn’t say anything, just smiled in agreement and blinked at her slowly. Rory blushed again, giving him one last hug and promising to see him later before she set off into the crowd. He watched her go, feeling his heart beat low in his chest. This felt like the end of an era. He was finished with high school now, which meant he didn’t need to stay in Stars Hollow any longer. His estranged father had shown up in the diner unannounced and although he left on Luke’s command, Jess felt like their story was only beginning.

Rory deserved to know everything about Jimmy and the way Jess was feeling, but she’d been so stressed about finals that talking to her was downright impossible. After finals, she’d practiced her Valedictorian speech on him and Lane, and he’d meant to talk to them both about it then but somehow it just never came up. Rory’s graduation had not been the right time to focus on himself, so he’d kept it all to himself then, too. And now? Well, today was _his_ day, so he could’ve sat her down to tell her everything but even that seemed like it was in poor taste.

Luke was holding a little get together for him at the diner. Nothing big. It’d be closed to everyone except those personally invited because Jess couldn’t be bothered to deal with all the townsfolk on a day like today. He wanted to be happy, he was _meant_ to be happy, and that was exactly why he’d spent the entire evening laughing with his girlfriend and his closest family and friends and didn’t give Jimmy Mariano a single thought.

When the diner started to clear out, Rory lagged behind and told her mother she’d catch up with her at home.

“Congratulations again,” she said once her and Jess were alone—Luke had gone upstairs some time ago.

Jess laughed. “You don’t have to keep saying that.”

She shrugged. “I know, but it’s fun because you start to squirm. I like it when you squirm.”

“Is that so?” He asked playfully and she nodded confidently.

“It is.”

“So, how come you decided to stay?”

Rory swayed on the spot, hands clasped behind her back. “I just wanted to spend some time with you.”

“The three hour party wasn’t enough?”

“Well," she started, taking a seat at the counter, "I was only here for an hour and a half out of three hours due to a very nice celebration with Dean and his family, so I have another hour and a half to make up for.”

Jess smiled and took a seat at the diner counter beside her. “I’m not complaining.”

“I didn’t think you would. Besides, Mom and I leave for Europe tomorrow evening and we’re going to be busy getting ready for that and I probably won’t get to spend much time with you until the summer is over.”

“Okay, so, what do you want to do?”

“Anything.”

“Anything?” He parroted, finding the answer odd.

“As long as I’m with you I don’t really care,” Rory said, smiling.

Jess grinned at her, twisting in his seat to look back at his old, beat up car outside the diner windows. “You wanna go for a drive then? Get some ice cream?”

“There’s ice cream here, isn’t there?” Rory asked, looking around the diner.

“Yes,” Jess confirmed. “But we don’t have any cones.”

“You do love your cones.”

“It’s just not ice cream without the cone.”

“Okay!” She hopped up from her seat and rushed to the door, twirling on her heel to face him. “Lets go get you some ice cream,  _in cones._ ”

 

 

**AGE TWENTY-THREE, APRIL. PHILADELPHIA**

“Hey,” Rory said to Jess just as she locked the front door behind her. “The loft seems quiet tonight, where are Chris and Matt?”

Jess kept his eyes on the book in one hand, sipping his beer in the most casual fashion he could with the other. “They’re staying out tonight.”

“Oh. Where are they staying?”

“Above Truncheon.”

Rory’s brows stitched together as she toed off her heels and hung her spring coat up in the closet. She put her keys on the hook by the door and carried her purse with her into the living room. “How come?”

“They wanted to give us some _alone time_ ,” Jess said, and now that Rory was closer she could see that he wasn’t happy at all. “They think we need to talk.”

She scratched at her nose and tried to busy her hands, looking through her bag for her phone. “What is there to talk about?”

“A lot of things, probably.”

“You have some ideas?” Rory asked curiously.

Obviously they’d had some issues over the past few months, but they’d buried the hatchet. She hadn’t been lusting after him quite as hard as she’d been before. Avery’s words served as a wake up call for her previous behaviour and Rory was doing her best to rectify the situation by not crossing over the line. No matter how she felt, she had to respect Jess’ feelings on the matter. Did rejection hurt? Yes, of course. She’d never been good with it, but she was learning now, and she cherished her friendship with Jess. It wasn’t worth ruining for a night, or a couple of nights of passion.

“A few.” He still wasn’t looking at her, but Rory didn’t entirely mind. “We can talk after dinner though. I’m not going anywhere.”

“Okay,” she said, proud of herself for sounding so casual even with the pit forming in her stomach. They may not have been dating, but there was nothing worse than hearing the Jess version of  _we need to talk_.

Rory shut herself in their bedroom and grabbed her pyjamas and a fresh pair of underwear from the closet. Her shower was as quick as she could make it without seeming like she was rushing, so she’d skipped washing her hair but took extra time on getting her body squeaky clean. When she was dressed and ready for bed, she slipped back out into the living room just in time to see Jess setting up an array of dim sum on the coffee table. She gave him a quick smile before sitting down and tucking one of her freshly shaved legs underneath the other.

“This looks good,” she praised. “Good choice.”

Jess hummed a fleeting note of thanks, but never actually said the words.

They ate mostly in silence, only talking here and there about her work day, his work day, and the book he was reading, but they were very short conversations that lapsed into awkward silences. When they were done, Jess cleared the coffee table and Rory took his book off the table and skimmed his notes in the margins. She almost felt bad doing it, knowing this was a rather private practice for him, but he’d always shared this part of him with her anyway.

When he came back, he propped one arm up against the back of the couch and leaned into his side, cheek resting on his fist. “You ready to talk?” He asked, and if she hadn’t known him she would’ve thought he was approaching this rather calmly, but she did know him and she knew he was nervous by the way he bit the inside of his cheek.

“Ready when you are,” she replied nervously, playing with the book in her hands.

“Okay. Topic one: Avery.”

Rory held her breath for two beats before letting it go. “What about her?”

“You’re curious about my relationship with her.”

She didn’t want to incriminate herself but she didn’t want to lie either. “A little bit, yeah.” She forced herself to stop there.

“I don’t know what we are. I don’t have any good answers for you.”

“Okay,” Rory said softly. She had no choice but to accept that. At least he was being honest with her.

“I like being with her.”

Rory bit her lip to distract from the wave of nausea that hit her. “That’s good.”

“I know she came to see you back in March.”

“She told you about that?”

“Yeah.” He rolled his shoulders back with a small sigh.

“…Were you…” She paused, trying to figure out if there was a better way to word her question. There wasn’t. “Were you mad at her for it…?”

Jess seemed pensive and he took a moment before he answered. “No. I wasn’t. I did feel like she overstepped, but I wasn’t mad. Annoyed, maybe, but not mad.”

“I was mad,” Rory admitted, still feeling a little ashamed. “I cried after she left. Angry tears. She just made me feel so stupid, but she also made me realize a lot of things that I wasn’t quite ready for yet. I’ve been unfair to you, and I knew that before she came but I wasn’t ready to acknowledge just how selfish I’d been acting. I’ve been trying really hard to just be regular Rory again because you deserve that much from me, Jess. I’m really sorry about how uncomfortable I’ve made you and my immature jealousy about Avery. You _like_ her, probably even love her and I should respect that as your best friend. No amount of attraction should make me behave in a way that could _hurt_ you. That’s absolutely not acceptable.”

He looked like he wanted to lean forward and comfort her, but they hadn’t had any real physical contact in months, and there was something else behind his eyes that she couldn’t quite place. She tried not to let herself wish for anything and refused to let herself feel disappointed when his hands or lips didn’t come anywhere near her.

“It’s okay,” Jess said. “I appreciate the apology and I’m sorry, too. I know this whole thing isn’t easy for you, either.”

“Fatal attraction sucks,” Rory joked, smiling weakly and receiving one just as watery in return.

“I wouldn’t say that’s what we have.”

Rory raised her eyebrows. “No?”

“No. I think we just care about one another so much we’re afraid of each other. That’s not a fatal attraction. We just suck.”

Rory laughed, looking down at his book still in her hands. She leaned over to place it back on the table and then she mimicked Jess’ posture so that they sat facing each other. “We don’t suck, we just don’t want to mess anything up. Which is good considering we almost did.”

“Yeah, we did.”

“Avery said that I… That I’ve never made you feel good enough.” She tried to find something, anything in his eyes, but he refused to take off his mask. “Is that… true? I’ve wanted to ask since that day but I never had the courage.”

“Yeah,” he practically sighed, sounding sad to admit it. “It’s true.”

Rory closed her eyes as the tingle of tears filled her sinuses. “I’m so sorry,” she whispered as a tear escaped.

Her bottom lip was quivering but she couldn’t control it, so she kept her eyes shut to avoid his gaze while she cried. Jess cupped her cheek with his palm and wiped away the tears that escaped. Rory leaned into him subconsciously, yearning for his warmth but also hating the way she always managed to make his pain about her.

“Don’t.” She pulled back and dabbed at her cheeks with the back of her hand, eyes open now. “I should be comforting you. I’m the one who messed up! Tell me what I did, tell me how to fix it.”

“Rory, you can’t,” he said and she took in a deep, shuddering breath. “What’s done is done. We can’t go back.”

She wanted to say something but her sobs wouldn’t allow her to speak. Jess stroked her bare shoulder with his thumb and moved in a little closer before pulling her to his chest.

“It’s okay,” he said, and Rory knew he was just saying it for her benefit. “I’m okay.”

“No, you’re not! I hurt you!” She spat out, disgusted with herself. “I hurt you and I didn’t even know!”

Rory felt his chest deflate as he exhaled, loud and deep. “So? It’s not like I’ve never hurt you.”

“That’s not the point!”

“Yes, it is, Rory,” Jess said firmly, pulling back to look at her. “That is _exactly_ the point. We’ve _both_ hurt each other and we have a lot of problems that stop us from moving toward in a way that we both might want. Maybe we’ll never get over those problems well enough to take the next step or maybe we will, I don’t know. What I do know is that you are my _closest_ friend, regardless of all the shit we’ve put each other through, whether it happened when we were seventeen or yesterday. All relationships take work, even friendships.”

“But I made you feel lesser than…”

He brushed her hair back and tucked it behind her ear. “Isn’t that how you’ve always felt in regards to Avery?”

Rory looked up at him, her chin digging into his chest. “Well, yeah but…”

“Then we’re even. I never meant to make you feel that way, either. But you still did, right?”

She nodded, letting her cheek rest against him as she listened to his heart beat. “I’m jealous of her.”

“I know.”

“I always have been. Not always _like this_ but at first I was jealous because she was taking you away from me, and then I was jealous because she seemed more mature in certain ways than me. When you broke up I was happy and that was an awful way for me to feel back then… You were so sad and there I was, lying to you whenever I tried to comfort you because I was _happy_ that she was gone. What kind of friend am I? What does that say about me?”

“It says you’re human, Rory,” Jess murmured before kissing the top of her head.

“No, I’m vile and wicked! Everyone at home has it all wrong. I’m not the princess in this story, I’m the witch!”

“Who says you can’t be both?” Jess said with a chuckle and she leaned back to glare at him.

“Not funny.”

“A little funny,” he countered, stroking her chin when she sighed at him. “Look, I hear you, okay? But you’re not the only one who was happy about breakups. I hated Dean for the way he ended things with you, but I was more than happy to see him go. And Logan? God, I had never been more proud of you when you turned that proposal down. I know you loved him, maybe you still do, but I was _extremely satisfied_  when you finally got rid of him.”

“You were?”

“I was.”

“Were you ever jealous of Dean?”

“Not of Dean, no,” he said.

She bit the inside of her lip. “Just Logan, then?”

Jess’ chest rumbled when he answered, his voice gravely low. “Yeah.”

Their little heart to heart had lasted almost until two morning, and by the time they were finished Rory’s eyes were rimmed with red and she’d started to fall asleep on his shoulder. Jess carried her to bed, careful not to wake her and set off to find his own blanket. When he came back, Rory was awake and sitting up but she still looked downright exhausted.

“I was wondering where you went.”

He held up the blanket in silent explanation.

“You don’t need that,” Rory said softly, and a chill ran down his spine. There was no sultry look to her, no air of seduction; she just looked small and innocent. “I won’t do anything, I promise. I just don’t like sleeping apart.”

Maybe it was a bad idea, but Jess dropped the blanket into the armchair by the door. He flicked off the overhead light and crawled underneath the bed’s regular duvet cover, basking in the warmth of Rory. She twisted on her side and snuggled in closer, laying her head on his shoulder.

He wrapped an arm around her waist and closed his eyes, letting sleep take him over.

 

**AGE EIGHTEEN, JUNE. STARS HOLLOW**

Rory didn’t know how long she and Jess drove around Stars Hollow for listening to music, discussing books and eating ice cream, but it didn’t feel like they’d spent enough time together when he dropped her back home.

“Come inside with me,” she said, sitting with her legs half out the door and her seatbelt off.

Jess got shifty-eyed in his discomfort, fingers drumming on the steering wheel. “I don’t think so. You and your mom have a lot to do before Europe tomorrow.”

“I want to show you the bag I packed,” Rory said with a smile. “You’d be proud of the amount of books I’ve stuffed into my pack.”

He perked up then, brown eyes alight with interest. She knew Jess couldn’t resist anything to do with books. “You’re going to lug around books in Europe?”

“I need reading material!” She defended before finally stepping out of the door, but she didn’t shut the door. “Come on, Jess. We’ll be extra quiet so we don’t wake up Mom.”

“I thought _I_ was the bad influence in this relationship? Your mother has got it all twisted.”

Rory giggled, feeling a little high on his words. She liked the idea of being the bad one a little too much. Jess was unpredictable, but she could be reckless, too. “Yeah, maybe she does. All the more reason for you to come inside so she can witness the truth.”

“Oh, Rory, Rory, Rory,” Jess tutted, shaking his head as he finally turned off the engine. “Don’t you know she’ll just blame me anyway?”

“I won’t let her. I’ll tell her it was all my idea and you were just my innocent little victim.”

“Yeah?” Jess stepped out of the car and closed the door just about as quietly as he could without alerting Babette or her mother. Rory quickly followed suit. “You’d protect me?”

“Always,” she promised, making her way around to him so they could cut over the lawn. He seemed to hesitate for a moment so Rory grabbed his hand and dragged him toward the porch like a child. “Besides, you’ve slept here before.”

Jess gave her a quick one shoulder shrug. “I just don’t want your mom to scalp me alive.”

“She won’t. I promised to protect you, remember?”

“I don’t want her to scalp you alive either.”

Rory sighed, staving off the guilt that bubbled in her stomach. “Your my _friend_ and I’m hanging out with you,” she argued, trying her best to sound logical. She slid her key into the front door and opened it up quietly, gesturing for him to whisper only now before she muttered, “She wouldn’t get mad if it were Lane, so she can’t get mad because it’s you. That’s hypocritical.”

“Rory, I don’t know if you know this,” Jess whispered back her, taking off his shoes with his hands before laying them onto the mat, “but, your mother _is_ hypocritical. She’s probably the queen of hypocrisy.”

“Hey,” she reproached, hitting him in the shoulder lightly. “Only _I_ can insult my mother.”

“My apologies,” Jess said sarcastically.

Rory smiled at him before making her way through the dark living room and kitchen and into her room. She flicked the light on and closed her door very, very faintly once Jess made his way in and then she turned to him, happy as can be when she noticed he’d made himself comfortable in her computer chair.

“So, where is this infamous backpack filled with all the books?” He wasn’t whispering anymore, though he still made sure to be quiet for her benefit.

“In my closet,” she said, making her way over to it and heaving it out with a groan.

Jess stared at her in amusement, his hand clapped over his mouth to silence his laughter. She glared at him. “I’m sorry,” he gasped, breathless from trying to stifle himself. “It’s just you can _barely_ drag that out of there, how the hell are you going to _wear_ it?”

“Like this,” Rory said indignantly, grabbing the straps and slipping them over her shoulders. She straightened out so everyone was aligned but her legs quivered under the weight and Jess watched her. Rory pushed herself forward to walk around until her knees buckled under the weight of everything and she yelped, almost toppling over. Thankfully, she found her balance on her bed and sat down on the edge of the mattress before she fell.

“Maybe you should take some books out,” Jess said, laughing harder now.

Rory glared at him. “But I’ll be gone for the _whole summer_ and I want to read these books before I go off to Yale. The people there are very well read and I won’t be the smartest anymore.”

“You’re already well read, Rory. You don’t need like forty books with you in Europe.”

She pouted. “It’s twelve.”

“Drop it to like… eight or something,” he suggested. “Twelve is still a lot of books.”

“Not as much as twenty, which was my original number. My mom wants me to bring nine, and I said I would if she only brought two tubes of toothpaste instead of three.”

“Why does she need three tubes of toothpaste?” Jess asked, but then he shook his head before Rory could answer. “Never mind, I don’t want to know. You can’t walk around with twelve books, you’ll die as evidenced by the show you just put on for me.”

Rory huffed, slipping the straps off of her shoulders. “Fine. I’ll bring it down to nine.”

“I’ll help you pick,” Jess said, getting up out of her chair and making his way to the bed. “Show me what you got, Gilmore.”

* * *

 

Jess wasn’t with her when she woke up the next morning, but she couldn’t remember if they’d fallen asleep in her room or not.

Her mother was in the kitchen with a plate of pop-tarts, her morning coffee and the paper. She didn’t so much as look up at Rory when she said, “Lover boy is on the couch.”

“You mean _Jess_?”

Mom shrugged. “Same difference, really.”

Rory took a seat at the table across from her. “No, not same difference,” she argued. “Jess and I were out late so he spent the night is all. It’s not a big deal. You act as if you found him naked in my bed with me or something. He’s on the _couch_ , Mom, which is like… at least twelve feet away.”

“Maybe Avery and Dean wouldn’t agree that it’s not a big deal.”

“Avery isn’t the jealous type.”

Mom looked at her then, the paper now down flat on the table. The look of judgment on her mother’s face was enough to shame her for a thousand life times. “But Dean is?”

“Mom, please don’t.”

“I’m just trying to understand, Rory. You agree that Dean wouldn’t like this if he knew of it?”

Rory shrugged, picking at the skin of her thumb. “Dean doesn’t like most things I do with Jess.”

Mom nodded. “And yet you continue to them.”

“That’s not _fair!_ He’s my friend, you _know_ he’s my friend. He was my friend long before there even _was a Dean_. I can’t just give up my friendship with Jess because Dean doesn’t like him and maybe because you still don’t approve even after all this time. I couldn’t do that anymore than I could give up Lane if you or Dean decided you didn’t like her. It’s the same thing.”

“Is it?” Mom asked, studying her.

Rory felt her face go hot but she willed the embarrassment away. “Yes,” she said firmly. “It is.”

“Okay. I’m sorry for questioning it then. Dropping it now and forever.”

Mom didn’t sound like was telling the truth, but Rory was willing to take whatever out of this conversation that was presented to it.

“ _Good,_ ” she replied, grabbing half of her mother’s pop-tart and running out of the kitchen to wake Jess as her mother called her a dirty, stinking thief.

Rory stopped as she caught sight of her friend curled up in a half-moon on the couch, his lithe form covered in a thin blanket. She made her way over to him and crouched down to get a better look at his face. His breathing was soft and his snores were something like whistles. She giggled at the sound as she poked his side.

“Jess, wake up,” she called to him and he groaned at her, twisting to face the other way. Rory poked him again. “Come on, Jess,” she pleaded.

He grabbed the blanket and pulled it up over his head. “Go away.”

She clutched the edge of the blanket and ripped it off him, laughing as he let out something between a fake-sob and a whine.

“Let me sleep.”

“You only have a total of four hours with me before I am required to go off to the airport.”

“Okay, see ya.”

Rory hit him and he grunted. “Don’t be rude. Get up and spend time with your best friend before she’s gone from your life _all summer long._ ”

“I’ll be here when you get back,” he mumbled.

“Fine,” Rory sniffed, turning up her nose at him even though he couldn’t see her. “I’m going to go shower and brush my teeth and if you’re not up by the time I finish then I guess I’ll just see you when I come back in August.”

Jess turned back to face her, eyes open as he grabbed his blanket back and bringing his knees closer to his chest. “Okay, see you then,” he saidand fell right back asleep.

 

 

**AGE TWENTY-THREE, APRIL. PHILADELPHIA**

When Jess woke up the next morning, Rory was still sleeping close to him, though they were no longer tangled up in each other. Jess moved slowly, relieved that Rory didn’t wake at the movement. He made his way into the kitchen to put on a fresh pot of coffee for her and grabbed a few eggs, some milk and cheese to make them both an omelette. For the first time since Avery left, Jess actually felt well-rested; it felt good to sleep side by side someone again in the simplest of terms.

There had been no awkward sexual tension for what seemed like the first time since Rory moved in. Their night somehow felt oddly nostalgic, a throwback to simpler times.

His phone vibrated against the kitchen counter where he’d left it last night. AVERY came up in big block letters and he answered the call with a quiet hello.

 _“Hey, sorry to call so early…”_ He turned to look at the time on the microwave; ten minutes to nine. Avery knew he typically wasn’t up for another hour at least. _“Were you still asleep?_

“No, no. I was up.”

_“Oh, good. I’ll get right to the chase, anyway. My mom’s hosting an art gala thing in a couple of months and she wanted me to put you and some of the Philly gang down on the guest list. I told her she can’t just do that without asking, so, of course, she told me I have to be the to one to ask. Typical, Mom.”_

Jess chuckled. “Yeah, sounds like her.”

 _“So… are you okay with being invited? I get that I’m asking you to speak for like three other people, but,”_ he imagined her shrugging and he smiled to himself, _“nothing I can really do about that.”_

“Send the invites,” he told her. “If some people don’t want to go I’ll let you know.”

 _“Okay,”_ Avery said, sounding relieved. _“Mom will be so happy. She’s excited to see you, Dad too, of course.”_

“It should be a good time.”

_“Never thought I’d hear you say that about a gala of any kind.”_

Jess smirked, leaning his elbows down on the counter. “Yeah, well. I’m unpredictable.”

 _“You really are,”_ Avery whispered and Jess licked his lower lip, dragging his teeth over it.

“When is this thing, exactly?”

_“August.”_

“Will I see you before that?”

 _“Do you_ want _to?”_

“I do.”

There was a pause on the other end before Avery said, _“Then I’ll check my calendar and get back to you.”_

Rory came out of their room rubbing the sleep out of her eyes with one hand and finger combing her hair with another. She yawned and took a seat at the kitchen table and mumbled good morning to him. He smiled at her, but kept his attention on his conversation with Avery.

"Just let me know," he said quietly.

" _Will_ do. _I'll be in touch._ "

"Okay," he said, pouring some coffee into a mug for Rory and placing it down in front of her. "See you soon. Bye."

When he hung up, Rory was staring at him curiously. "Avery?" She asked and he nodded just as he grabbed a bowl for the omelettes and put the pan on the stove. "Is she coming to visit again soon?"

"She's going to try."

"That's nice," Rory said, and for once Jess didn't hear an inkling of jealousy. "I'd like to see her again and apologize for the way I've acted toward her lately. She deserves that."

"That's very mature of you," Jess said, cracking an egg into the bowl before pouring in a bit of milk.

"I'm an adult. I should act like one."

He looked at her over his shoulder with a smirk. "You're an adult? Huh. Who knew?"

"Shut up!" She cried, but she laughed all the same.

Jess found himself smiling as he poured the egg and milk mixture into the pan and watched it cook, pulling up the edges so it would cook evenly. He hadn't counted on last night being so productive in terms of his relationship with Rory, but he made a mental note to thank Matt and Chris later, so long as they didn't make it a habit to start meddling. He glanced over to his best friend every so often, watching as she took quiet sips and stared out the kitchen window into the spring morning with a ghost of a smile.

 

**AGE EIGHTEEN, AUGUST. STARS HOLLOW**

When Rory returned from Europe there was a letter resting on her pillows.

She knew Jess’ handwriting anywhere, but was more than a little curious as to why he’d left her a letter of all things. The very first stop her mom and her had made on the way back home was Luke’s, but Jess hadn’t been there. When she asked Luke about his whereabouts he’d given her an extremely vague answer of, “Oh, you know Jess. He’s unpredictable that kid. Who knows where he went.” Which didn’t seem like so much of a weird answer at the time, but after finding this letter on her pillow, Luke’s answer almost seemed like a cover up.

Rory tore the envelop open and scanned the contents. It was a very short letter.

_Dear Rory,_

_I’m sorry for not telling you this sooner, but my dad came into town a few weeks ago and I’ve decided to follow him to California. If you have anymore questions just ask Avery._

_Hope you had a good time in Europe and if things go well I’ll see you when you’re all settled in at Yale,_

_Jess._

She’d stared at the letter for far too long, reading it over so many times that the words were practically seared into her brain. Jess had been the person she’d wanted to see first the very moment she’d gotten off the plane. Being away from him for the entire summer had proved to be a much harder challenge than she’d thought, especially considering all the fun they’d had on their last night. In a lot of ways, Europe had made her question her feelings for Jess. She couldn’t bring it up to her mother, knowing full well she’d been judged for her confusing swirl of emotions, but she couldn’t help wondering if there was something to be said about missing Jess far more then she’d missed Dean.

She waved the letter in her mothers face when Lorelai asked what was wrong, but she didn’t cry. She _refused_ to cry. She was _done_ crying over Jess Mariano.

“Maybe talking to Avery about it _would_ be a good idea, hm? She’d know more, that’s why he put her in the letter for you.”

“ _No_ ,” Rory said, ripping up the letter in her fury and throwing the pieces into the air. “If he really wanted me to know all the details he would’ve told me himself, not through a horrible letter which basically said _please redirect all questions to a customer service representative_. Who does he think he is?! I’m supposed to be his _best friend_ and he just runs off to California without even telling me! He didn’t even tell me that he _met_ his dad! What kind of friends are we if we can’t share important details?!”

Mom twisted her lips up in that way she did whenever she disagreed, but Rory wasn’t ready to listen to any of her mothers so-called logic.

“I’m leaving.”

Mom stood up and followed her to the front door. “And just where exactly are you going to go? Do I need to worry about my air mile points?”

“Oh please, Mom!” Rory snorted, slipping on her shoes. “I’m not going to run off to California and chase after Jess. I am _never_ chasing after him again, in fact. I’m going to go see Dean, my _boyfriend_ , the one boy who will actually be excited to see me and has been waiting for my return all summer long. The boy who doesn’t lie straight to my face. The boy who _actually_ cares about me!”

She didn’t give her mother the chance to say anything else before she was out the door and off to Dean’s house. Rory stood on his porch, trying to regulate her breathing before ringing the door bell. His mother answered with a polite smile and polite questions about Europe before calling Dean down. Her boyfriend greeted her with a great big hug that made her feel loved and a kiss that made her head feel fuzzy.

Rory pushed him back toward the stairs with what was hopefully a sultry look, and given by the way Dean’s eyes darkened she had to have done something right. He laced their fingers together and raced up the stairs with her trailing behind. He shut his door and she grabbed him by the shirt, spinning him to push him down on his bed and straddle his lap.

“Am I the first person you came to see when you got back?” He asked as she trailed a series of kisses down his jaw and neck.

“Yes,” she whispered. It wasn’t _technically_ a lie.

Dean grinned and pulled her all the way on top of him as he leaned back. “Missed me that much, huh?”

She kissed him to shut him up.

 

**AGE TWENTY-THREE, APRIL. PHILADELPHIA**

When Matt and Chris returned sometime in the evening, they had Jenn and Val in tow.

"Hey!" Matt called out, holding up two bags of alcohol when he came into the living room. "We were gonna pregame and then go out to a club tonight or something, you guys in?"

"Shh," Jess said, pointing to a sleeping Rory; she had her legs thrown across his but she was propped up by a ton of pillows at the end of the couch. 

"Oh." Matt winced. "Sorry."

Chris, Val and Jenn spread themselves out in the kitchen, looking for glasses quietly.

"I guess you guys worked things out?" Matt asked, taking a seat beside Jess.

Jess shrugged, looking away from Rory and to his roommate. "Yeah, I guess."

"Good." He nodded. "So we did a good thing then?"

"Yeah."

"Heheh," Matt cackled quietly. "See, Chris and I are the  _good types_ of meddlers."

"Maybe Chris, not you," Jess said, smirking. "Never you."

Matt pouted just as Rory started to wake up, her hand rubbing at her eyes the same as this morning. She pulled her legs back from Jess and stretched her arms up high.

"Oh, sleeping beauty awakes!" Jenn called out from the kitchen.

Rory groaned in confusion, blinking at Matt before rising up to look over the couch at Jenn. "When did you guys get here?"

"Just now," Matt promised. "We're gonna go out to a cluuuub. Wanna come?" Rory looked at Jess, worry evident in her brow. Matt seemed to catch on too, because he quickly added, "Or not! No worries."

"No, it seems fun but I really think I'm all partied out."

"Same," Jess agreed. "You guys have fun though."

"Won't you at least join us in the pre-game?" Jenn begged. 

Jess looked at Rory for the answer. "One drink won't hurt will it?"

"I guess not."

He got up and pushed Matt up with him, not wanting him to have the time to talk to Rory alone. "You want a rum and coke?" He asked her, eyeing the Malibu and Coke cans on the counter. He grabbed her a glass when she said yes, and eyeballed about one ounce of the liquor before diluting it with about half a can of Coke. He handed it off to Val who gave it to Rory and then he set off to grab a drink for himself. He found a few tallboys in Chris bag and asked if he could take one. 

"Knock yourself out," Chris said and Jess popped the can open.

He found himself back on the couch eventually, and Val took a seat next to him. "You sure you don't want to come?" She asked, leaning in close.

"I'm sure."

Val sighed in defeat and leaned back into the couch. "Okay then. I guess I'll just have to look for another boy tonight."

He didn't know if she was trying to make him jealous or not, but he didn't care either way. He took a sip of his beer and glanced at her out of the corner of his eye. "That's probably for the best," he said. He could've told her in plain terms that whatever relationship they'd had last year was over, but he figured she'd get the hint eventually. His life was complicated enough without adding another girl into the mix, especially when he couldn't care less about about being Valerie Marquez's boyfriend  _or_ personal sex toy.

Rory pressed her feet into his thigh to get his attention and when he looked at her he found her trying to suppress a laugh. He flicked her knee lightly and closed his eyes just before taking another sip of beer. It felt like a weight had been lifted off his chest.

 

 


	5. Chapter 5

**Notes for the Chapter:**

> Two updates in one day!! I'm on a roll. I honestly just really want to wrap up the Dean/Avery years and get to the Logan years, but yay for Jess making a real effort here! Also I couldn't resist using some S4 dialogue, mainly because I like how heated Rory gets in that scene, I thought it'd be fun to flip it and have Jess be like "...girl...wtf"
> 
> ANYWAY as always, leave a comment on your thoughts below!

**AGE TWENTY-THREE. MAY. PHILADELPHIA**

Rory sat in her favourite cafe, at her favourite table waiting patiently but nervously. Having lunch with Avery might have been the worst possible idea Rory ever had. They weren’t friends, had never been friends, and possibly would never _be_ friends. The only good thing about this situation was her choice of meeting place. She felt at ease here in front of the fire place, even though it was coming up summer (and May was more hot and humid than she'd ever remembered it). It also helped to have Jenn within sight, so at least if apology went awry she'd have a friend to turn to.

There was no reason why things _shouldn't_ go well, she told herself. Avery was mature and emotionally stable in a way that Rory felt she could really only dream of being. She blamed her mother for raising her this way, unable to control the contempt she felt when she realized other girls her age didn’t have such inappropriate relationships with their mothers and were better off for it. Rory loved her mom more than anything in the world, but she wasn’t blind to the ways in which by being raised a young mother directly contributed to some of her larger failures in life.

“She’s here,” Jenn whispered to her as she walked by and Rory sat up taller in her chair, scouting the cafe.

She smiled when she caught Avery, waving to her awkwardly.

“Hey,” Avery said unbuttoning her spring jacket; she looked pretty, as usual, even though she was covered in a light sheen of sweat. “Sorry I’m a bit late. Philly is still a little confusing to me, and wow, is it ever _hot outside_ today. Someone should tell mother nature that it's only the middle of May. Were you waiting long?”

Rory laughed, understanding Avery's struggle with the weather and Philly streets all too well. “No, I wasn't. I just got a got of coffee and came to sit down. Come, sit, sit!”

Avery took her invitation and draped her jacket on the back of her chair, purse resting in her lap. “So, how’ve you been?”

“Good, good,” Rory said, trying to sound casual but polite. “How about you?”

“I’ve been well. A little busy with work, lots of clinical trials and things but it's nothing I can’t handle. How’s work for you? I remember a few months ago you were upset about something?”

Rory blushed. “I’m surprised you remember that.”

“Why wouldn’t I? You told me, I listened, and therefore I remembered.”

“Has anyone told you that you’re possibly _too_ nice?”

Avery smiled. “My last boyfriend broke up with me for that reason.”

“Oh," Rory said, feeling guilty. "Sorry.”

“It's okay. He was kind of a dick. I’ve kind of sworn off relationships because of him, actually.“

Rory traced the rim of her cup, wiping off the lipstick print with her thumb. “What was he like? Other than dick-ish, I mean.”

“Just very… mean, I guess. He just wanted me to view the world a certain way and I couldn’t. I told him as such but,” she shrugged, “he wouldn’t let go. He made me feel guilty for being myself and not the girl he wanted to me to be.”

“That sounds awful.”

“It was. But he’s out of my life now and I’m happier.”

“I understand that feeling.”

Avery leaned forward to rest her elbows on the table. “Which ex are we talking about here?”

“Both of them, I guess. I was sad when the break ups happened, but the longer I’m without them the more relieved I feel. Dean and I were so toxic, and Logan and I weren’t much better. Jess and I are…” She sighed, looking away from Avery and to the special’s board. “We were kind of unhealthy, too, if I'm being honest. So much pent up frustration and hurt.”

“But that’s fixed now, right? Jess said you two had a very lengthy talk and a lot of problems stemming from way back when were addressed.”

Rory nodded. “Yeah, we had a really nice heart to heart and got a lot of things out of the way. We’re good now, happier. We apologized for hurting each other in the past and recently..”

Avery reached over the table to still Rory’s hand and she gave it a gentle squeeze. “Good. That’s good.”

Rory stared at their clasped hands, unsure of how to react.

“Sorry,” Avery said, pulling her hand back. “I’m known for overstepping personal boundaries sometimes. I’m working on it.”

“No, it’s okay… I didn’t mind. It was nice. Comforting.”

“So, putting my personal boundary issues aside... I’m sure you didn’t just invite me here to chat. Not that I’d mind if you did, in fact I’m open to it if you are. Might help to become unlikely allies?”

Rory went back to tracing the rim of her cup and she bit her lip to keep from smiling too wide. “That _would_ be nice, but, no I invited you here so I could apologize to you.”

“For?”

“For everything, really. I was jealous of you when we were in high school. Jess was my best friend, we spent a ton of time together and then you came in and suddenly Jess wasn’t spending as much time with me anymore. He prioritized you, and fell in love with you, and I was upset that you even existed. I know that sounds childish, but it’s the truth.”

“Are you still upset that I exist?”

“Not so much anymore, no,” Rory said with a small smile.

Whenever Avery laughed, her nose did a cute little wrinkle thing that Rory kind of admired, and this time was no different. “That’s good then. So, are we on our way to being unlikely friends?”

“I think we just might be.”

“I’m glad,” Avery said, grinning from ear to ear in a way that made Rory blush. “Now, lets talk about literally _anything_ but Jess.”

 

**AGE EIGHTEEN. OCTOBER. STARS HOLLOW**

Getting back to Stars Hollow from California was fucking exhausting. Jimmy and Sasha had been nice enough to buy him a plane ticket, but there had been delays and a connecting flight, and by the time he made it in, it was almost midnight. The diner was closed, but Jess let himself in by using the key at the top of the door and quietly made his way upstairs.

Uncle Luke was asleep, snoring away peacefully on the other side of the apartment and Jess dropped his bag on the floor and crawled into bed with his clothes on, too exhausted to do anything else.

When he awoke the next morning, Luke was gone and he could hear the bustle of the diner patrons He rubbed at his eyes, wandering into the bathroom to wash his face and brush his teeth. He took out a change of clothes from his drawers and and stripped down before hopping back into the bathroom to take a quick shower. Once he was clean he made his way down, ignoring the glares and angry murmurs from the townsfolk as he grabbed an apron and put it on without thinking twice.

“What are you doing?” Luke asked him.

“What does it look like?”

Luke studied him. “When did you even get back? I woke up this morning and you were there. Didn’t even move when I tried to wake you.”

“Sorry, I was tired. Long travelling day.”

“I have to warn you,” Luke said, looking around the diner. “Everyone here is kind of out for your blood.”

“Really?” Jess asked, eyes wide in mock surprise. “I coudn’t tell by the way they were all glowering at me and saying _There he is, the boy who broke Rory’s heart!_ They do know I’m not her boyfriend, right? And what the hell did I even do!? Sorry that I went off to go and get to know my father. God! She’s so infuriating! Everything is always about her. Well, what about me, huh? She doesn’t give a damn, does she?”

Luke didn’t have the time to answer as Lorelai made her way through with the sound of the bell, pausing to stare at Jess. She shook the shock off a moment later and made her way over to the counter.

“So, the golden boy has returned.”

“That I have,” Jess said, putting his usual bored tone of voice back on. He willed himself to calm down from his earlier outburst with a few shallow breaths.

“Did you call Rory?”

“I just got back.”

“I meant when you were in California. Did you call Rory then?”

Jess sighed, not really wanting to think about this. “I tried after I knew you guys were back from Europe. It just went straight to voice mail.”

“She’s still mad you,” she said, almost as if this were news to her but she was also impressed. “Wow, that girl can hold a grudge, maybe she really is related to Emily Gilmore.”

He knew Rory was mad; he hadn’t told her about going off to California in person, and he hadn’t told her about his dad. It’d been a really bad decision to let her find out via letter when she came home from her dream vacation, but he was never very good at doing things properly, anyway. Besides, if he’d told her, she would’ve spent her entire vacation worrying about him and spending all her money on calling cards just to talk to him, and he just didn’t see the point of putting either of them through that. She should’ve been happy he even left her a letter.

“Of course she’s related to Emily Gilmore, she’s her grandmother,” Luke said drily, picking up his order pad. “Are you gonna get something or just harass my nephew?”

“I like harassing your nephew,” Lorelai said gleefully. “He’s so fun to annoy.”

Jess rolled his eyes and grabbed the pot of coffee, setting off to give refills anyone in need.

“So, my parents are having a great shabang for Rory’s birthday this year,” Lorelai told him when he made his way back around the counter, “since they know I get dibs on her twenty-first they’ve made it a point to lock down nineteen _and_ twenty... You should come.”

“Didn’t you just say Rory was mad at me?”

“ _Yeeees_ ,” Lorelai said very slowly as if he were stupid, “but she’s also _Rory,_ and she’d love to see you. Lane would, too. She’s not quite as mad, I don’t think.”

“Lane actually picked up the phone when I called,” Jess confirmed. “We talked sometimes.”

“Mrs. Kim allowed that?”

“She did after Lane begged enough, I guess.”

“Ahhh,” Lorelai nodded. “Yes, the ol’ puppy eyes. Even Mrs. Kim is not immune. Good to know.”

Jess laughed, though it was short lived. “Don’t think it’d work if you tried it.”

She pouted at him. “You don’t know that!”

“Trust me, I know. Mrs. Kim’s only weakness is Lane. No one else can get through.”

“You’re probably right,” Lorelai sighed, looking dejected but she perked right back up a moment later. “So, party?”

“I hate those Gilmore parties, you know that.”

“I do. I do know,” Lorelai giggled evilly, “and that’s exactly why you should come. Someone else will hate being there more than me! My mother can rag on and on about you and totally forget about my existence! How grand!”

Jess sighed.

“Plus, Rory _will_ want you there once you two talk this out.”

“Fine. I’ll think about it.”

 

**AGE TWENTY-THREE. MAY. PHILADELPHIA**

“So, I hear you and Rory are friends now,” Jess said to Avery as he looked around her tiny hotel room. She'd went with a different company this time, and he wasn't sure if he liked it. It seemed seedy, and he was kind of worried about her safety with the shoddy lock and chain. God, he was turning into Luke.

“Turns out we have a lot in common other than just you.”

He nodded. “I know. You’re very similar in certain ways.”

“You should bring her to the art gala.”

“I figured there was an invitation for her in that stack you gave me,” he said, looking toward the dresser where the four royal blue envelops sat.

Avery gave him a bemused smile. “There _is_. I meant you should bring her as your _date_.”

“My date?” He repeated. “I don’t think that’s a good idea, we just got back on track as friends. I don’t want things to get weird again.”

“Ugh, Jess,” Avery groaned laying back on her bed with her arms spread out wide. “Don’t you get that things were only weird because you weren’t exploring your attraction like _normal people?_ You know what I do when I find someone attractive? I ask them out on a casual coffee date, and I get to know them and see if I like them.”

“I already know Rory though.”

“You’re so dense,” Avery said, sitting up to glare at him. “Yes, you know Rory but you don’t know Rory intimately. How can you determine if she’s The One if you don’t get to know her that way? I know you said you were scared, but sometimes you have to take the plunge.”

“I thought I told you I don't believe in all that _The One_ stuff. It's really a little to _Liz Danes_ for me. Besides, even if I do decide to do that… that means you and I will be—“

“Over,” she finished for him before he could say it. “Yes, you and I will be over. I would say we could keep this up, but Rory’s a very monogamous kind of person, and if you want to explore being with her, you really have to _be_ with her. So, let the gala be your first official fancy date. If it doesn’t work out then at least you gave it a shot. But, if you keep running away you’re going to be stuck with Rory Gilmore as your biggest _What If_ in life. Do you want that?”

“No.”

“Didn’t think so. So, don’t let it happen. Date her, kiss her freely, hold her hand. See what it’s like, see how you feel.”

He laid down, staring up at the light fixtures. “What if it’s great?”

Avery laughed, laying down beside him and folding her arms beneath her head. “I don't think I've ever heard anyone ask that with such a negative connotation.”

Jess kept silent, unsure of what else to say. He had a lot of feelings swirling around and day by day it seemed harder to identify them and compartmentalize.

“If you’re worried about me,” she said as if reading his mind, “don’t be. I wouldn’t be encouraging you to go after this if it was breaking my heart or something. We should be honest with ourselves about what this thing between us even is.”

“What is it?” He genuinely wanted to know.

“It’s a security blanket. We’re comfortable with each other, so falling back into our old relationship rather than pursuing new one’s is easier, and that’s not bad per se. Seeing each other brings up a lot of old memories and we haven’t changed much so we just pick up exactly where we left off. It’s not like you and I ever broke up due to a lack of love—that was never our problem.”

He found himself agreeing with that, but he didn’t voice it, wanting to hear more of her opinions. “So, what's our problem then?”

Avery turned to look at him, eyes smiling. “I don’t really know, but I do know that we’re able to live without each other.”

“I can live without Rory, too,” Jess said truthfully, “She’s my best friend, but I can live without her. I don’t _want_ to, but I can.”

“And there’s the key,” Avery whispered, voice filled with pride. “You don’t _want_ to live without her. That’s the important part, Jess.”

“You say that as if I wanted to live without you… I didn’t. I still don't.”

“I know,” Avery said, looking away from him and up at the ceiling but he kept his eyes on her profile. “You know when people say stuff like _I need you_ it’s misconstrued as being romantic whereas _I want you_ is somehow perverted and selfish? I think the two should be switched. To _need_ someone is selfish, but to _want_ someone? That’s so romantic. To say _I can live without you but I don't want to_ is so much better than being unhealthily attached, don't you think?”

She turned to look at him again when he didn't answer her, this time there was a smile on her lips to match the one in her eye.

“You do  _want_ Rory, right?”

He looked away from her this time, fixing his eyes back on the light. “Maybe. Probably.”

“You should make an effort to get everything you _want_ out of life, Jess.” She got up from the bed and handed him the four royal blue envelops from the dresser. “Don't hide behind _maybe's_ and  _probably's_. You have to have conviction. Just promise me you’ll at least think about asking her as your date?”

Jess sat up, taking the invitations from her and admiring the smooth gloss finish on the paper. “Okay.”

 

**AGE EIGHTEEN. OCTOBER. YALE**

A knock came at their dorm door early on a Friday, and Rory groaned in bed. “Paris, get the door.”

Paris’ mattress squeaked as she flopped onto her back. “What am I? Your maid? You get it.”

“Paris, we both live here!”

“So?! I need a full eight hours of sleep, Rory. We don’t all wake up looking perfectly angelic and beautiful.”

Rory groaned, stuffing her face under the pillow as another loud knock filtered through. She squeezed her eyes shut, hoping for sleep to overcome her once again. Whoever it was could just come by later, but then her phone started to buzz on the night table and Paris yelled at her to shut it up. Rory reached for the device without once opening her eyes, hand flailing as she hit the table corner and hissed. Her phone stopped ringing and she left her arm lay limply over her mattress edge.

Then the knocking started again and Paris shot up next to her with a very loud and very angry, _“OH MY GOD!”_

She heard her roommate stomp out into the common room and open the door so violently it banged against the wall so loudly that Rory winced.

“What are you doing here, Kerouac?” She heard Paris say and finally her eyes shot up and she removed her head from her pillow.

“Is Rory here?”

“Yes she’s here, and the both of us were trying to _sleep.”_

 _“_ It’s like twelve in the afternoon on a _Friday_ , don’t you have class?”

“Oh, great,” Paris said sarcastically, “the boy will no ambition has the audacity to judge the women trying to liberate their minds. Typical.”

Rory sprung up out of bed and ran her fingers through her much shorter hair, glad not to find any tangles. She loitered around the door just before she heard Jess coming closer.

“She’s in here right?”

“You can’t just barge into a person’s room like that! Were you raised by a pack of wolves?”

“Yes. Also, that’s ironic coming from you considering your tendency to just barge into people’s _houses_ ,” Jess retorted drily, and Rory smiled before mentally slapping herself. She had to stay strong in anger. “Rory. Are you awake? I want to talk to you.”

She could’ve pretended to be asleep, but Jess was pretty well-known for being relentless when he had something to say and she _did_ want to hear what stupid excuse he’d managed to come up with in the three months they’d been apart. Finally, she gave in and opened the door to him, telling Paris to wait outside.

“Oh, great! Locked outside _my own room_ so that you can fuck Bukowski! I won’t forget this, Rory!”

Rory rolled her eyes just as she shut the door and leaned against it, crossing her arms over her chest as she took Jess in. His hair was longer now then she’d ever seen it before and she couldn’t decide if she liked it or not; it seemed to be a weird in between stage.

“What do you want?” She asked coldly, staring him right in the eye to let him know she meant business.

Jess stared back at her. “I wanted to apologize. Maybe tell you about California and my dad if you’re interested?”

“Really? Because I’ve thought of this moment quite a lot since you left. What would Jess say to me if I ever saw him again, I mean he just took off—no note, no call, nothing!”

“Except, I did leave you a note, and I did call. You just didn’t pick up because you’re petty!”

“And then three months go by,” she continued on as if she hadn't heard a word he said, “no word, _nothing_ , so he couldn’t possibly have a good excuse for that, right?” She knew this only proved that he was right with the petty comment, but she didn't care.

“Rory, you’re being unfair.”

“Oh, _I’m_ unfair?!” She squawked in disbelief, tightening her arms around chest. “You’re the one whose unfair! I would’ve listened, Jess. I would’ve been there for you but you didn’t _tell me anything!”_

“I didn’t want to ruin your trip to Europe! Sue me.”

“You’re penniless, suing you wouldn’t be beneficial to me.” She could feel her resolve weakening, he was hard to stay mad at.

He gave her a wry smirk. “You’d probably lose more money taking me to court.”

“Probably,” she said, averting her gaze from him now. “How’d you know where I lived, anyway? This campus is huge.”

“I asked your mom. I kind of couldn’t wait til tomorrow to talk to you.”

“My mom hates you, why would she give you my address?”

Jess shrugged. “Hey, I’m just telling you how I got here. She also invited me to a birthday party your grandparents are throwing you.”

“She did?”

“Yep.”

“Are you going to come?” She asked hopefully, smiling when he nodded in affirmation. “Yay!”

“Wow, you forgave me quick this time. Took you almost a full two months to talk to me when I accidentally knocked your book off the bridge.”

“It’s the hair,” she joked, “it’s really working for you.”

He ran a hand through it and shook it out like a dog, causing Rory to giggle a little even though she didn’t want to.

“Okay,” she said, moving away from the door to sit in the middle of her bed. “Tell me about California and your dad, and don’t spare a single detail if you know what’s good for you.”

 

**AGE TWENTY-THREE. MAY. PHILADELPHIA**

“I need to find a dress for the gala,” Rory said, digging through the closet. “What colour should I wear?”

Jess listened to her with half an ear as he read, but he didn’t have it in him to respond. He wasn’t good with women’s fashion, and Rory was picky.

“Jess!” She threw a stuffed animal at him, something he didn’t even know she had in that mess of a closet. “Help would be nice!”

“You look good anything,” he said easily. “Just have your mom make you something.”

“I don’t have time to go back to Stars Hollow for a fitting!” She cried. “Do you know how long it takes to make a ball gown?”

“Nope.”

Rory sighed in frustration. “Of course not. Well, it takes a long time and that’s why I can’t have my mom make me a dress.”

Jess flipped to a new page. “Okay.”

“You’re the worst friend ever!”

“Hey,” he warned, putting his book down to glare at her. “You’re lucky I’m even in here while you go about this chaos.”

Rory flopped down on the bed next to him. “You wouldn’t leave me to do this alone. I need your opinions, I want to look good. All the women are going to be decked out in makeup and jewels and pretty dresses. I want to stand out.”

“You always stand out,” he said, still looking at her. “Your personality is great, people flock to you because you’re a welcoming and calming presence. You even look like an ethereal woodland creature, sometimes it’s very surreal. You’re gorgeous. And very charming.”

Her cheeks were red when he’d finished and she curled up into his side. “You’re being nice,” she mumbled into his shirt. “Why?”

He thought back to his conversation with Avery and pursed his lips, suddenly feeling parched. He could ask her to be his date now, but it didn’t seem quite like the right time. There was something he wanted to do first. “Wasn’t it you who once said that best friends are supposed to be nice?”

“Well, yeah, but you’re being like _extra_ nice. You’ve only ever called me a woodland creature once.”

Jess swallowed against a hard lump in his throat, his palms suddenly felt very sweaty. He’d done everything in his power to forget about that one night, but of _course_ Rory would remember it. “I don’t recall,” he lied and Rory pushed herself up on her elbow to inspect him.

“Don’t lie,” she said simply, smiling.

“Not lying.”

“You totally remember.”

“I don’t,” he denied.

“I can refresh your memory.”

Jess groaned. “Please don’t.”

“Ah, so you do remember,” she teased.

“I didn’t say that.”

“You didn’t have to.”

He looked at his book, committing the page number he was on to memory before closing it and placing it onto the floor. “You’re not planning on bringing someone to the gala, are you?” He asked, regulating his breathing so he didn’t hyperventilate from nervousness.

“No. Why?”

“Can you… maybe keep it that way for a while?”

“I wasn’t planning on going with anyone at all, honestly. I thought we were all going as friends. Unless Matt and Chris are bringing someone? Oh, Lane did drop a hint about wanting to go. Maybe Chris will bring her, that’d be cute right?”

He nodded. “Very cute.”

“Okay, back to you and why you’re acting weird. What’s going on?”

“I can’t say quite yet.”

She narrowed her eyes at him in interest. “I’m not going to pry, only because I’m interested to see where this is going to go.”

“Good,” he said, breathing a little easier. “You’ll find out soon if all goes well.”

“If you’re setting me up on a blind date, or we’re gonna go on a double date to this event I’ll be _very_ upset with you.”

He laughed, leaning in close to her ear and whispered, _“I promise it’ll be a good surprise.”_

 

**AGE NINETEEN. FEBRUARY. STARS HOLLOW**

In February, Jess was reunited with his mother. It’d been an unexpected visit. She’d come into the diner with some new man of hers, and Jess had heard her and Luke talking about something or the other. He knew his mother’s voice anywhere. It made his blood run cold, and his chest tighten. He hid out in the storage room, trying to regulate his breathing and fight against his flighty instincts. Whenever Liz Danes was near him, he _had_ to run.

“Jess?” Caesar called out. “Jess, your uncle is looking for you. Says there’s someone hear to see you.”

Jess bowled right past his uncle’s right hand man and practically ran to the back door of the diner. “Tell him I’ll be back later.”

“But Jes—“

Whatever it was Caesar had said, Jess didn’t hear as he was out the door before he’d even finished.

He hadn’t talked to anyone about his problems with Liz, and even if he wanted to he couldn’t. Rory was away at Yale, and it didn’t quite seem worth it to drive the whole 22.8 miles out to see her over something so stupid. Avery was in class, and he didn’t want to distract her. Senior year was important, especially for her. All her classes were at the IB level, which Jess heard was somewhat harder, or at least just different from AP. He watched her stress over homework and tests in the four months he’d been back home, and while he tried to comfort her, he wasn’t exactly the best at it.

Avery was a lot like Rory when she was stressed, she preferred to be alone and stress out without anyone to witness it, and Jess did his best to respect that, but it’d put a growing distance between himself and his girlfriend that felt larger than the distance between Stars Hollow and Venice Beach. She was right there and yet she felt so far away.

He took a seat at his bridge, fiddling in his pockets for a cigarette and wound up frustrated when he remembered that he’d quit over the summer under Sasha’s demand. He bit his lip hard enough to draw blood and pulled his most recent book out of his back pocket, believing that fiction would be much better than reality.

The school bell pulled him out reading a couple of hours later, and he didn’t even realized how numb his hands were until he was snapped back to reality. He stood up with a shaky breath, wondering if he should wait for Avery or not. He swiped his tongue over the wound he’d inflicted on himself and made his way toward Stars Hollow High.

Avery was walking with a group of friends when she spotted him. She said her goodbyes to them and ran over to him, greeting him with what he thought was a much needed hug. He held her to him even when she tried to let go and she relaxed against him before wrapping him up tighter. “What’s wrong?”

He pulled back, licking his wound again. “My mom’s here.”

“Your _Mom?_ ” Her eyebrows shot up in the same way they had when he’d told her about Jimmy. “Wow, life isn’t giving you any breaks.”

“Zero.”

“Did you talk to her?” She asked and he shook his head. “Did you see her?”

“No, I just heard her. She came with some guy named TJ apparently. Boyfriend number a thousand by this point.”

“I’m sorry.” Avery caressed his cheek with a gloved hand. “Do you want me to come with you to the diner, just incase she’s there? I can act as a buffer. Mom’s love meeting their son’s girlfriends.”

“I don’t want you to meet her. She doesn’t deserve to see any part of my life. Not you, not Rory, not Lane, not even Paris.”

“Are you sure?” She looked worried and he didn’t like seeing that directed toward him so he leaned down to kiss her. “That’s not an answer,” she said with a smile.

“I’m sure,” he answered.

Avery wrapped an arm around his back as they headed toward the town square. “Okay. Walk me home?”

 

**AGE TWENTY-THREE. MAY. STARS HOLLOW**

The Crapshack looked the way it always did with its wide porch and hanging flowers, Lorelai’s jeep in the driveway. The only real difference was the neatly manicured lawn that Jess knew had to be Luke’s doing in the end, because Lorelai had always kept her lawn marshy for as long as he could remember. Jess sat in his car, staring up at the house, now slightly larger after all the renovations Luke put into it, and he tried to talk himself into just making it onto the porch _at least._

He knew why he was here and what he needed to do, but even though he was getting better at facing his fears he still was a runner at heart.

But, he’d made the drive all the way down here and there was no better time like the present.

Jess opened up his door and pushed himself out of his car and up to the door, knocking hard twice.

Luke was the one to greet him with a look of shock. “Jess!” He cried, opening his arms up for a hug and Jess reluctantly went in, patting his uncle firmly on the back.

“Uncle Luke.”

“I didn’t know you were coming by.”

“Surprise visit.”

Luke nodded as if that made sense to him. “Come inside.” He stepped to the side to let Jess in, gesturing toward the living room with his arm. “t’s hot out there. I don’t want you to get heat stroke.”

The sun had almost completely set, but there was still a gross, sticky humidity in the air that reminded him of the old Summer Festival with those singing barber shop-looking boys. This was the type of heat he’d always associated with Stars Hollow. He stepped into the Crapshack and relished in the feeling of the air conditioning against his skin.

“Is Lorelai around?” He asked. “I saw her car in the driveway.”

“Ah, yeah, she’s just getting ready for bed,” Luke explained, making his way into the kitchen as Jess followed at his heels. “She’ll be excited to see you. You hungry? I can make you something.”

“No, I’m okay. And I highly doubt that Lorelai will be pleased to see me,” Jess scoffed, “especially not after she hears what I have to say.”

Luke turned to look at him, lips pressed into a frown. “Why? What is it you have to say?”

He looked away, unable to handle Luke’s scrunity, “I’d rather wait for Lorelai.”

“I’ll go get her then,” his uncle said warily. “You stay here. Don’t bolt.”

“Why would I bolt?”

“Hey,” Luke put his hands up in surrender, “I never know with you. You’re skittish.”

When he was gone, Jess took a seat at the table and drummed his hands against his thigh. Rory’s old room was right in front of him and though her door was closed, Jess imagined it as a time capsule of sorts. Lorelai wasn’t the type to get rid of anything pertaining to her one and only child. Everything Rory made or owned was precious and had to be kept exactly where she’d left it, assuming she hadn’t emptied out her entire room upon moving to Philly.

There was a part of him that wanted to go in there, but he felt weird snooping even _if_ Rory was technically his best friend and _other._ The latter was the whole reason why he was here. Things with Rory had calmed down, but that didn’t mean the war waging on his heart had. He kind of knew where he stood, and now he knew where Rory stood (kind of), but he didn’t feel comfortable thrusting them forward into anything new without talking to Luke and Lorelai first.

Luke came back into the kitchen before Jess could dwell any longer, his wife trailing behind him and mumbling something about how she still didn’t believe that Jess was here. She stopped in her tracks when she saw him and he offered her a polite, tightlipped smile.

“Wow, you really weren’t kidding.”

“I told you I wasn’t,” Luke said gruffly. “Jess says he has something to say to the both of us.”

Lorelai cocked her head to the side. “What is it?”

Jess wiped his sweaty palms against his jeans. “It’s about Rory.”

Panic flashed behind Lorelai’s eyes and she glanced back at Luke before looking back at Jess. “What about Rory? Is she okay? It has to be serious if you’re here in person and not calling. Did she get fired? Oh god, she got fired just like she was worried about and she was too scared to tell me! She’s been in a depression, hasn’t she? That’s why she hasn’t been calling and always cuts our conversations short. I just thought I’d give her space, you know? Give her a little time to herself to come around but now you’re here and obviously that had to have been the wrong decision for me to make, but I just thought after the whole Yale thing that I—”

“Lorelai,” Jess interrupted. “Rory’s _fine_. She didn’t get fired.”

“She didn’t?” Lorelai asked, sounding relieved. “Oh, thank god! What’s wrong, then?”

“Nothing’s _wrong_ ,” Jess said. “I just… wanted to ask you both something and it’s kind of old fashioned and not really my style at all, but I _have_ to ask or else I’ll never get the courage to do this.”

“Oh god,” Lorelai breathed, looking at Luke in horror. “He wants to marry her. My mother was right, they’ve been living together in sin and now she’s pregnant with his baby!”

“Lorelai would you please just let him talk!? I’m sure he doesn’t want to marry Rory and I’m sure she’s not pregnant with his baby,” Luke contested, crossing his arms tight over his chest. “You don’t want to marry Rory because she’s pregnant with your baby, do you?” Suddenly not sounding so sure.

“No,” Jess said, rolling his eyes in frustration. How was this even an option? “I don’t want to marry Rory, but… I do want to date her.”

“See!” Lorelai cried, grabbing her husbands arm. “Living in sin!”

“We aren’t living in sin!” Jess argued, patience waning. There had been that one night back in March, but they hadn’t even actually had sex, so it hardly counted in his mind, even if she had reached a climax through grinding on his thigh.

Lorelai appraised him, lips pursed. “Why do you want our permission for this?” She asked seriously. “I’m sure Rory would date you regardless of if I approved. She was certainly your friend without my approval, moved to Philly without it, too. Moved in with you without it. And now, after all of that, you come here asking for my permission?”

Jess shrugged a little, knowing damn well it was as stupid as Lorelai made it sound. “Rory cares about what you think. You approved of Dean, and disapproved of Logan. She’s experienced both sides of the coin with you and now she’s stuck in the middle.”

“Did she say that?”

“No, but I know.” He rubbed his hands on his pants again, trying to psych himself up for this next part. “Rory and I have been friends for a really long time but lately we’ve been sort of toeing the line between that and something else and it’s caused a rift. We’re fine now, but nothings _really fixed._ The attraction is still there and it’s just going to pile up again until we explode and we’ll continue down this path of fighting and making up and then fighting again. Honestly, that’s just not how I want things to be.”

“So you want to give it a real shot,” Lorelai filled in.

“Yeah, I want to see if we could work. It’s complicated, I’m not denying that, but I think we owe it to ourselves to try it out.”

“I think it’s a good idea,” Luke chimed in, blushing when Lorelai and Jess both turned their eyes on him. “You and Rory… The feelings have _always_ been there. I’ve seen it, even when the two of you were blind to it yourselves, it’s why I gave you that talk when you were sixteen. My big mistake was never letting you know that I actually supported the union.”

“You what?” Lorelai asked. “You never told me this!”

“Because I knew you’d be mad! You liked Dean, but I never liked him. He wasn’t good enough for her and god knows Logan was a real piece of work, but Jess is my nephew and I know him and I see what Rory sees in him and I always thought they were good for each other. I knew you wouldn’t agree so I kept my mouth shut.”

Lorelai hummed, glaring at her husband before turning back to Jess with a much softer look. “Do you love her?”

“I think you know the answer to that.”

“I know you _love_ her, but are you _in love_ with her?”

“I don’t know,” Jess admitted. “I think I’d like to find out though.”

“And what about Avery? Rory told me she was back in your life. We still do talk about _some things_ you know.”

“Avery is back in my life, yes.”

“Rory doesn’t do well with open relationships, Jess. You can’t force her to be something she’s not.”

“I wouldn’t even bother to try.”

Lorelai sighed, letting her shoulders droop forward. “So, you’d end things with Avery completely before pursuing Rory?”

“That’s the plan.”

“And you’ll be kind to her?”

“I’ll do my best.”

Lorelai looked at Luke and rubbed her thumb over her bottom lip. “What do you think? Is he being genuine?”

Jess rolled his eyes as Luke really seemed to consider the question. “I think he’s genuine,” his uncle said finally, looking straight him. “He has my blessing.”

“Okay,” Lorelai said, squaring her shoulders off and fixing Jess with a fierce look. “I can’t lie and say I like this because I don’t. I really, _reaaaally_ don’t… I mean I’ve watched her cry over you more than once, and so if you hurt her again, I’ll have to kill you.”

“I expect no less.”

“But,” she continued on as if she hadn’t heard him, “I suppose I can give you my blessing for this because it’ll make Rory happy. She’s wanted this for so much longer than she’s been willing to admit.”

“Me too,” Jess confessed, feeling a little light headed from actually obtaining Lorelai’s blessing.

“How long?”

Jess blinked. “What?”

“How long have you wanted this?” Lorelai clarified.

“Oh.” Jess ran his tongue over his teeth. “Since I was thirteen, but then I shelved it. Didn’t let myself feel it again until I was twenty.”

Lorelai gave him a real smile then. “Then I guess it’s about time, huh?”


	6. Chapter 6

**Notes for the Chapter:**

> Say goodbye to Dean, y'all!! 
> 
> Well, at least for the most part. He'll probably be back a few more times, but he's no longer Rory's bf and we're moving into the Logan years! As always, don't forget to leave me a comment about your thoughts!

**AGE NINETEEN. MAY. STARS HOLLOW**

Liz barged in to the diner in a whirlwind of cannabis, cigarette smoke, and her weird woodsy perfume. Jess wrinkled up his nose at the scent, trying his best to keep himself calm in the face of an impending anxiety attack. He had been dealing with his mother on and off for months now after she’d showed up in Stars Hollow unannounced back in February. There were talks of her moving here, but nothing concrete had happened yet and Jess hoped it never would.

She kept trying to act as if everything between them was fine. She bragged about him to townsfolk but insulted him in the same breath by saying how _difficult_ he’d been before he came to this town and how _hard it was_ to raise him all on her own. She never took accountability for the fact that she was never home, leaving him to fend for himself and starve for days on end. Liz took the credit for him turning out so well, boasting about how it’d been her idea to send him to his uncle even though she knew damn well that Jess had run away in the middle of the night with nothing but a duffle bag filled with books, music, and some clothes.

Her lack of self-awareness infuriated him, and while he’d always thought his mother was selfish, he was now starting to think she was downright cunning.

He avoided talking to her by going around and giving everyone coffee refills and making sure their food was satisfactory. Thankfully, Liz didn’t seem interested in talking to him anyway, though he did hear his name come up more than once. Luke caught his eye from behind the counter and gestured for him to head upstairs for the remainder of the night. Jess gave his uncle an odd look but he did as he was told.

Once alone, Jess took off his grimy, diner-smelling clothes from the day, hopped into the shower and got himself ready for bed. He’d once disrespected his uncle’s line of work, but he held a new found respect the service industry after working in it full time now. He was saving up for his own place, and he thankfully wasn’t too far off. He’d learned to make it in this town, but he was dead set on getting out sometime. Rory had, and Avery would be following suit in a couple months as well. He couldn’t be the one left behind (well, there was Lane, too, but he always felt as if she were trapped here by life circumstances).

When he emerged from the bathroom, Luke was sitting at the their small kitchen table with some dinner looking pensive.

“Why the long face, _Uncle Luke?_ ” He said, ribbing him a little. “Liz Danes got ya down?”

Luke frowned at him. “A little bit, actually, yeah.”

“What’d she do now? Let me guess, she went to a casino and blew all her life savings, which is actually just whatever savings she didn’t spend on weed or booze yet. Or, she did spend it all on weed and booze and needs _more_ money for weed and booze!”

“She’s gettin’ married,” Luke filled him in, voice sardonic and dry. “To that… _guy_. I mean, I know she claims he makes her better and keeps her on track, and I mean I _have_ seen a change but… marriage, really?”

Jess shrugged, flopping onto his bed and getting comfortable with his book amidst the propped up pillows. “Won’t be the first and I doubt it’ll be the last.”

“She wants you there.”

“Pass,” Jess said, cracking open _The Wars_ by Timothy Findley. Rory had been getting into Canadian Literature recently due rereading _The Handmaids Tale_ by Atwood, and her reading habits typically bled onto him as well. They’d decided to have a little bet to read all the famous Canadian classics and see who could remember the most details and recite the most lines. It was a fun way for him to pass the time.

“Jess…” Luke sighed. “I know your relationship with your mom is a little _complicated,_ but all she’s asking for is that you walk her own the aisle. Is that really so bad?”

Jess stared at his uncle in disbelief, _The Wars_ placed protectively on his chest. “Tell me you’re joking. Not even two minutes ago you couldn’t even believe she was getting married to TJ and now you’re trying to convince me to go? Make up your mind!”

“I just think it would be nice and not that big of a deal in the long run.”

“Okay, so I’ll go to the next one.”

“Jess, Liz thinks TJ is different… and maybe she’s right.”

Jess scoffed, putting his book back to his face. “She thinks all the guys are different. I’m not interested, Luke.”

He heard Luke get up, his chair scraping against the tile of the apartment just before his shadow loomed, spilling over the Timothy’s words. “I’ve seen TJ with Liz, Jess. They seem to work, even if I am a little skeptical and think they’re rushing the whole marriage thing. We need to support this thing, give it a real chance.”

“No,” Jess said harshly, “we don’t.”

“I don’t want you to regret this.”

Jess sneered at the pages before him. “I doubt I will.”

“Jess, don’t be selfish here, okay? I know things are difficult between you and your mom but she loves you and you love her.”

He had enough. Jess dog-eared the page he was on and slammed his book shut before leaping off the bed, searching the apartment for his duffle bag.

“What are you doing?” Luke asked.

“I’m leaving,” Jess said, checking under the bed and feeling relief when he saw his bag. He grabbed the strap and pulled it toward him, throwing it on top of the bed as he stuffed some clothes into it. “I can’t listen to this anymore. I don’t have to do _anything_ for Liz. She’s never done anything for me and I thought that you, of all people, understood how I felt. After all you took me in, raised me, and yet _still_ I have to sit here and listen to you defend her?

“ _She left me_. She left me at home for weeks on end without food. I came to you without having had a proper meal in over _two weeks_ and you want to _defend her?_ You call _me_ selfish?! I’m the victim, or do you not care anymore because I’m almost twenty and not a child you have to protect anymore? Little Jess is all grown up now, so he should just put up with his piece of shit mother, right?”

Luke went red at the accusation and he spluttered to get a defense out as Jess threw his book on top of all his clothes and pulled his bag shut by the strings. “I just think that maybe, maybe this is Liz’s turning point, you know? This could be _the moment_ where she turns her life around! Don’t you want to be with her to witness it? To show her that you forgiven her?”

Jess slung his bag over his shoulder and gave Luke a vehement glare. “I haven’t forgiven her. I will _never_ forgive her!” he shouted, storming out of the apartment and down to his car. He shoved his bag in the passenger seat moving jamming his keys in the ignition and taking off without a second thought.

 

**AGE TWENTY-THREE. JUNE. PHILADELPHIA**

Rory’s phone rang against the bathroom counter as she took a shower, and she quickly shut off the water, wrapped herself in a towel and picked it up with a breathless, “Hello”. She hadn’t even bothered to check the caller ID.

“Rory, hey!” Luke’s distinct voice came from the other line.

Rory fixed her towel and made her way out of the bathroom and into the bedroom, smiling at Jess’ sleeping form. “Hi, Luke! How are you?”

“Oh, I’m great. I was just calling because Jess didn’t pick up the phone and I wanted to make sure he wasn’t dead in a ditch somewhere.”

Rory grinned against her device, leaning down onto the bed to check just how asleep Jess was. She ran her fingers through his hair and he twitched before his eyes opened up to look at her curiously. She shook her head, retracting her hand so she could point at her phone just as she mouthed, _‘It’s Luke’_. He groaned at her and drifted off to sleep again.

“He’s very much so alive,” Rory confirmed. “He’s just taking a nap.”

“Ah, okay,” Luke said. “So… How are things with you?”

“Good, good,” Rory said, getting off the bed to go and find some clothes. It was rare that Luke ever called her. They loved each other, but they weren’t prone to having a ton of long lasting conversations, as evidenced by the awkwardness in Luke’s tone. “Just getting ready to go out.”

“Oh! That’s nice. You and Jess have a date?”

Rory froze at that, twisting to look at Jess on the bed in confusion. He couldn’t see her, nor could he hear their conversation—or, at least not Luke’s part—but she couldn’t help but direct her bewilderment at him all the same. “No,” she said slowly. “Why would Jess and I be going out on a date?”

“Because you’re dating now, aren’t you?” Luke said, sounding just as confused as she did. “He came and talked to your mom about it last month. I assumed the two of you were already together by the time he’d asked us for _permission_ , kind of.”

“He did what now?”

“…You didn’t know he did that…”

Rory shook her head, mouth agape in shock. “Nope, I can’t say I did.”

“I’m sure he was planning on telling you eventually. He just wanted to make sure your mom and I would be okay with it. It was kind of uncharacteristic for him, he seemed really nervous. Are you mad?”

“Not at you,” Rory said, voice clipped as she stared hard at Jess. “Can I call you back?”

She could practically hear Luke wince. “Don’t kill him, okay? I’d like my nephew in one piece. I don’t say it a lot, but I love that kid.”

“I love him too,” Rory admitted, though she was still angry. “He just might come back home a little bruised, is all.”

“I’ll pray for him.”

 

**AGE NINETEEN. MAY. YALE**

Rory didn’t know what to make of Jess showing up in the middle of the night with tears in his eyes.

She’d never actually seen him cry before, and the moment she opened up the door to him he’d collapsed on her shoulders. He was a strong, silent crier. He didn’t blubber or get weird, his voice hardly even changed though it definitely cracked sometimes. Rory led him over to the couch and stroked his hair, whispering sweet nothings because she didn’t know what else to say. Jess held onto her so tight she thought she was going to burst, but she kept her composure and peppered his forehead with soft little kisses until he’d finished telling her exactly what had happened. It was a lot of information to take in.

“Come with me to my mom’s wedding, please,” Jess begged. She hadn’t seen such desperation and fear in his eyes since, well, _ever_. “I can’t face her alone.”

Rory didn’t know what to say. The fact that Jess was so terrified of his mother almost terrified _her_. Jess was like her knight in shining armour, he’d always protected her from just about anything she’d been afraid of, and she’d never seen him scared. If a Princess’ knight was scared, was she to be scared, too? Or was she to to become the knight for a day? The latter seemed to be the better option in her mind. Liz Danes didn’t scare Rory Gilmore.

Growing up, she’d let herself fester hatred for the woman who abused and neglected her best friend, and while that feeling hadn’t changed in six years Rory _had_ always thought of Liz in a very particular manner and what she’d been met with wasn’t it. She’d always imagined Liz Danes to be cold and unfeeling. Super strict. The type of woman you would just immediately hate on sight, but the Liz Rory had met was eccentric, bright and lively. Her paraphernalia was hippie-ish with it’s feathers, gem stones and shiny bright metallics. She seemed like the kind of woman who would be a _good_ mother if you didn’t know the truth, and the way she went about interacting with Jess in front of people almost made Jess seem like a liar.

But Rory knew he wasn’t lying.

“Why are you even going, Jess? You don’t have to go if you don’t want to.”

No matter how nice Liz seemed on the surface, Rory knew the truth. Jess had come to Stars Hollow gaunt and exhausted at age sixteen. He had an electric-shock fence around his heart and didn’t let anyone get close to him at all in the first few months, not even her. It’d taken a lot of relentless, hard work to get Jess to open the gates to her again, and a person didn’t just turn out to be so guarded for no discernible reason.

“Luke asked me to…” He didn’t have to say anything else.

Rory had never really been mad at Luke before, but she supposed there was a first for everything. Jess shouldn’t have been made to feel like he needed to be there by the man who took him in. Luke should’ve understood Jess’ feelings for his mother and let things be, but even though Rory loved Luke very much, she knew that he could be a bit of an enabler.

Luke gave Jess a lot of tough love, which Rory was sure Jess needed sometimes, but she often worried that maybe he was being a little bit _too_ harsh. Especially when he didn’t seem to be harsh on his alcoholic, drug abusive, child neglecting little sister. The thought of it made her blood boil—that Luke could ignore Jess’ feelings on the situation and prioritize Liz, who didn’t even _deserve_ a warm welcome back into Stars Hollow after everything she’d done.

Maybe Yale was making her feel a bit disillusioned with her home town, but she just didn’t get how _everyone_ , including her own mother, could label Jess as the devil but talk on and on about how _nice_ and _sweet_ Liz Danes was. It all made her feel sick.

 

**AGE TWENTY-THREE. JUNE. PHILADELPHIA**

Jess awoke with a start when he felt something soft and fuzzy hit his head. He was breathing hard as he sat up, looking for the item that had assaulted him, and he found a stuffed animal of Rory’s on the floor—the same one she’d thrown at him a month ago while deciding her gala options well in advance.

“What the hell?” He asked, voice thick with sleep as he rubbed at his eye. “What was that for?”

When his vision cleared, Rory was standing in font of him with her hands on her hips and her chest heaving. Her skin was red and blotchy in her anger and she was only dressed in a towel, though her skin seemed dry.

“Why are you mad at me?”

“ _Why am I mad at you?!_ ” Rory repeated, voice so high it could shatter glass. She threw her hands up in the air as she began to pace around their bedroom. “I’m _mad_ at you because Luke just called and said that you went to Stars Hollow to talk to him and _my mother_ about dating me!”

His stomach dropped and flipped. He sat up a little straighter, bringing his knees to his chest and locking his arms around them protectively like a little kid. “Oh,” he said dumbly, not knowing what else to say other than _‘Oh, shit’_ which was repeating itself so loudly in his head he couldn’t think of anything else.

“ _Oh?!_ That’s it! Just _‘Oh’_. God, Jess, do you know how fucked up that is?!”

He tried to shake himself out of the fog and produce an intelligent sentence. “Uh, kind of?” Okay, so not entirely what he was going for, but it was better than his previous response. His brain still wasn’t fully awake, so he was having a rather difficult time piecing together what was going on.

Rory snorted, angry and loud. “ _Kind of_ , he says. _Kind of_!” Jess bit his lip and moved to get off the bed, but she pointed at him with a very loud, “Ah-ah-ah! You stay there, don’t come near me.”

“Rory—“

“Nope! No way! You’re not going to _Rory_ your way out of this one,” she said, still pacing, hands wringing in her typical nervous habit. “I need time to process this because I’m having a hard time believing that you actually drove from Philly to Stars Hollow to talk to _my mom_ about dating me, but you never told _me_ that you wanted to date me. And that’s the funny part, Jess! Luke _assumed_ we were dating! He was asking if I was getting ready to go on a _date_ with _you!_ Needless to say, I was very confused. Why on earth would I be going on a date with Jess, I wonder? Oh, because apparently I’ve _dating him for a month_ and I didn’t even know about it!”

Jess pinched the bridge of his nose, dragging in a deep breath and fighting off the straight up craving he had for a cigarette. He hadn’t smoked in years, but stress brought the need back full fucking force. “Rory, please, you’re giving me a headache.”

“I don’t care,” Rory said childishly and Jess sighed.

“Rory, come on. At least let me tell my side of the story?” He pleaded, rubbing at his temples.

She went silent, stopped pacing, and her face told him that she was thinking it over, but then she started up again. “No. Not yet,” she said, rubbing at her lower lip. “I need time to process.”

“You already said that.”

“Well, I’m still processing!” She snapped.

He nodded, finally getting himself out of bed. “Okay, well, while you’re processing, I am going to go shower and get ready for Chris’ birthday celebration. Tell me when you’re ready to have a two-way conversation.”

 

**AGE NINETEEN. MAY. YALE / STARS HOLLOW**

Liz Danes was getting married tomorrow and Rory didn’t know how to feel about it. Technically it was none of her business, but the whole thing was really upsetting Jess and therefore it was upsetting _her_ too. It’d been at least a week since Jess and Luke’s big fight, and Jess had yet to go home—not that Rory was complaining. Yale had sort of become his home away from home and it was actually really nice to wake up to his sleeping form on the couch. Paris complained of course, but Tanna and Janet didn’t seem to mind him as much as they’d minded Lane.

Rory tossed and turned with a sigh, unable to sleep due to an overactive mind. She pushed herself up and wandered out into the common room to find Jess still awake on the couch, his lower half covered in a blanket, and an old, worn book in his hands which she recognized as _The Old Man and The Sea_. He’d finished _The Wars_  the first night he’d spent here and they’d talked about the bird symbolism at length until around three in the morning and they fell asleep together on the couch. She would’ve rolled her eyes at his current reading choice had she not known Hemingway was one of Jess’ biggest comforts when he was feeling blue.

“Hey, do you mind if I watch some TV?” Rory asked him, feeling a little timid. “I can’t sleep…”

He looked up from dear ol’ Ernest and pulled his legs up to his chest so she could fit on the couch. She smiled at his silent gesture, taking a seat before reaching for the remote and tried to find something kind of interesting, or at least amusing, on television.

“How come you can’t sleep?” He asked, keeping his voice quiet so he didn’t wake her other three roommates. Always so thoughtful. “You still stressed about that paper for your first year seminar?”

“No, no,” Rory said, trying to reassure him that she was not on the verge of a mental breakdown. “You actually really helped with that. Your relentless mocking of the educational system helped me to formulate my thesis on _The Turn Of The Screw_.”

Jess smirked. “Glad my cynicism was useful.”

“Don’t get used to it,” she teased.

They fell into comfortable silence for a couple of old episodes of The Simpsons, Jess’ book forgotten on the floor. He shifted to bring his legs over the edge of the couch so Rory could move in closer to the television. She laid her head on his shoulder and he wrapped an arm around her back, neither one of them saying a word as Homer strangled Bart.

 

* * *

 

The only good thing about Liz’s wedding ceremony was that it was comical.

The renaissance theme was a rather nice aesthetic, and it _was_ fun to see the town all dressed up like a festival, but the actual ceremony was a little ridiculous. Rory had opted to sit next to Jess once he’d finished walking his mother down the aisle and they had a rather difficult time keeping themselves together. Jess snorted beside her every time TJ said something about tights, and Rory nudged him with her knee but she kept her lips pressed inside her mouth to keep from laughing.

Liz and TJ had good taste in food as well as music, but Rory decided it was better not to dance on her own. Dean hadn’t come to the event, citing work and college papers as his reason and Rory was more than understanding. Avery came a little later, having missed the whole ceremony but got to enjoy the reception. Rory sat with her and Jess at the table, feeling a bit like a third wheel, but she’d found Lane in the commotion and they talked for a bit until Mrs. Kim demanded her daughter come home, fearful of what kind of drugs the wedding goers were on.

 _Reflecting Light_ started to play just as Rory watched her mother and Luke make their way out onto the dance floor, and she watched them with a dreamy look, thinking that they looked rather sweet together. She was still mad at the both of them, really. Jess hadn’t told her about his _other_ fight with Luke back in February that’d resulted in his mother yelling at him in the streets of Stars Hollow, but she’d found out anyway when Gypsy let it slip.

Her mother had apologized to her but not to Jess, and Rory found that even more infuriating. Still, at least her mom and Luke looked happy tonight.

“Looks like they’re enjoying themselves,” Jess said to her, leaning into her personal space so she could hear him a little better.

She nodded, still watching them with a smile. “Yeah, they are.”

“You… uh, wanna dance?” He asked her and she looked at him to find his nose wrinkled and cheeks tinged in embarrassment.

“You dance?” She asked, looking at him increduously. “I’ve never seen you dance.”

“Doesn’t mean I can’t,” he argued.

Rory laughed and then took in the empty seat beside him. “Where’s Avery?”

“She had to get home. She’s going on a road trip to check out Columbia officially tomorrow.”

“Oh!” Rory perked up at the mention of school. “That’s exciting! Is Columbia her first choice?”

“Nah. UMASS is. She likes their microbiology program the best.”

“But, that’s so far away,” Rory said, feeling a little sad for Jess. He was going through enough already without the thought of losing his girlfriend to distance. She’d been worried about her relationship with Dean, too, when Harvard had been her first choice but things had worked out well in the end when she’d decided upon Yale. Maybe Avery would decide to go somewhere a little closer, too.

Jess shrugged a little, trying to look unbothered but Rory could see right through him. “I have a car, I’ll drive to see her sometimes.”

Wordlessly, Rory got up out of her chair and held her hand out to Jess. “Come on, let’s dance,” she said, hoping that it would be a welcome distraction.

They swayed comfortably together in the moonlight, their bodies pressed close. Rory had her arms resting on his shoulders and he held onto her waist as they moved. He actually hadn’t been kidding when he said he knew how to dance. His movements were effortless in comparison to her stiff ones, but she didn’t mind, she just tried to enjoy the moment. They’d made it while _Reflecting Light_ was still playing and but stayed for another song, this one more upbeat in rhythm and tempo.

Jess removed her arms from his shoulders to take one of her hands and spun her out to the beat and she spun back in with flushed cheeks.

“I didn’t know you were a flashy dancer, too!” Rory cried, struggling to catch her breath. She was suddenly thankful that her dress was flowy and the furthest thing from constricting as her chest heaved.

Her friend grinned, grabbing her tighter by the waist with a small shrug. “I’m having fun.”

“Me too.”

He spun her again, this time with his arm sweeping above her head. She’d been prepared for it and she gave a little twist in her kitten heels, enjoying the rush of the warm wind against her skin. When she made it back into his arms she was grinning, latching onto him in her dizziness. They slowed for a moment so Rory could relax and she stared up at him unabashedly.

“You look handsome,” she flirted, feeling free to say whatever she wanted without the aid of alcohol.

He smirked at her. “Why thank you, Miss Gilmore. You are looking quite beautiful tonight as well. That dress is…” He whistled low to show his appreciation

“This old thing?” she asked in a very bad southern accent, batting her eyelashes with a giggle as she looked down at her blush pink dress. “I just found it in the back of my closet.”

Jess snorted, but his eyes went dark and serious just a moment later. “You look like a woodland creature.” She raised her eyebrows at him, imploring him to continue with that train of thought.“You know… Ethereal. Sometimes I just look at you and wonder how on earth you’re real,” he admitted, cheeks red in the twinkle lights of the wedding.

Rory beamed at him, though her face was burning up. “You honestly think I’m that pretty?”

“You know you’re that pretty,” Jess mumbled.

She tightened her grip on his shoulder and leaned in close until her cheek was resting against his. “Thank you,” she whispered, not feeling even a little guilty about how light she felt inside.

 

**AGE TWENTY-THREE. JUNE. PHILADELPHIA**

“I can’t believe we found a club that’s actually hosting a full fledged, Hip Hop and R&B Night on my birthday!” Chris shouted, sounding more than a little excited.

“Only the best for little Chrissy,” Matt cooed, moving in to pinch his cheek.

Lane laughed, standing up on her tippy toes to kiss her much taller boyfriend. “Yep, only the _best_ indeed.”

Jess smiled at the scene, but didn’t join in on teasing the birthday boy.They were all waiting to get inside the club. It was hot out, real humid for late night, and Jess felt a little envious of the girls wearing practically nothing tonight. He’d always thought they were kind of insane for their club wear, especially in the winter months, but he understood it all too well in the summer. If he could get into the club without a shirt, he might’ve thought about it.

Rory was standing in front of him with Jenn and Val, wearing a tight fitting white dress that stopped just above her ankles, but its sex factor came from the fact that it hada very, very low cut back _and_ front. Val had found it in her closet and demanded she wear it out tonight. Rory had seemed embarrassed at first, glancing back at Jess a bit of self-consciousness, but he hadn’t paid her any mind as he spritzed his cologne on his wrist. He watched, from the corner of his eye, as Rory’s face turned dark, her anger at him returning every few moments as if she’d forgotten that she was supposed to be mad at him. That was the only thing that’d given him hope for a possible reconciliation tonight.

In the end, Jess assumed she wore the dress out of spite, and he had to admit that he didn’t mind.

The club was hot and sticky when they got in and offered no relief from the humidity outside. Matt had at least thought ahead and reserved them a booth so that they didn’t have to stand on the dance floor with a ton of people. The bass of Rihanna’s S.O.S drowned out his own thoughts and the words of his friends. He slid into the booth, noting how Rory sat across from him rather than next to him and conversed with anyone but him. He wondered how long she’d be mad for, and if he should try his luck.

“I’m going to go get a drink,” he announced, loud enough for everyone to hear but he still pointed to the bar anyway. He slid out from his seat on the end and leaned in to Rory’s ear. “You want a vodka cranberry?”

She leaned away from him, glaring with a mix between ice and fire. “I can get it myself,” she said, pushing him back and stalking off without him. He watched her go into the crowed with a silent groan but he didn’t regret trying to start a conversation.

Chris was looking at him in disbelief, his lips pursed into a very judgmental frown. “Really, man?! Again?!”

Jess shrugged, feeling helpless. He’d really thought he’d done the right thing by asking Lorelai’s permission. He knew how close she and Rory were, and the last time Lorelai hadn’t approved, it’d caused some major problems between them. Jess just hadn’t wanted that to happen again, but he’d never expected Rory to react quite like _this_. He was more than a little curious to her adversity, wondering if she just didn't like that he'd avoided talking to  _her_ first (a total valid reason for anger, really), or if it was something else completely.

“I’m gonna fix it,” he promised. “What do you want to drink? Your first two rounds are on me.”

The rest of the night was actually kind of nice, aside from Rory’s attitude and how gross and grimy he felt in this club due to the heat. Everyone had cleared out the booth to dance, leaving Jess and Rory alone in the booth, but she refused to look at him and instead focused on her refreshed drink.

He slid around the booth to get a little closer to her, and she glanced at him them but she still didn’t really acknowledge him. She swayed in her seat to the beat of _Bossy_ by Kelis, laughing as she watched Jenn and Val grind on each other and playfully push away any guys who tried to get in on the action.

“You ever going to talk to me tonight?”

She still didn’t look at him. “I’m talking to you right now.”

“Yeah, but you’re still mad.”

“I’m allowed to be mad about what you did.”

Jess nodded, leaning in closer to her so she could hear him. “I’m not saying your feelings aren’t justified, I just don’t know _why_ you’re so upset.”

Rory looked at him over her shoulder, their faces so close that it wouldn’t have taken much leaning to kiss her, but he respectfully moved back. She was mad at him, and he was going to let her be mad if that’s what she wanted. “Lets talk outside.”

“If we go out, we can’t come back in.”

“It’s late anyway,” Rory said, looking at the time on her phone, but he couldn’t read it. “And I’m getting tired. Walk me home and we can talk.”

“Let me find Chris first. Stay here, I’ll be right back.”

He set off into the crowd, weaving in and out through the dancing crowd and avoiding the hands of patrons who tried to pull him to them. Finally, after what felt like at least five minutes, he found Chris and Lane by the DJ, pressed together as they swayed to the smooth beat of Buttons by the Pussycat Dolls. Didn’t seem like a song that either of them would be into, but Jess wasn’t about to judge anyone’s drunk tastes.

When he let them know he and Rory were leaving, they both cried out in disapproval, but Lane sobered up quickly as she realized this means they’d get the chance to talk. She shooed him off, consoling Chris as he cried about Jess abandoning him on his birthday, and Jess thanked her as he went back off to find Rory, wishing Chris a final happy birthday.

He found Matt on his way back to Rory, his friend was at the bar chatting up two women and pat him on his shoulder as he passed, letting him know he was done for the night. Matt didn’t pout or cry like Chris, too distracted by the women in front of him, and he simply said, “Alright man, see you at home… Or not.”

When he finally got back to the booth, Rory was saying her goodbyes to Val, Jenn, Lane and Chris (who had miraculously made it back before he had). They left as soon as Rory hugged everyone and they set out into the late night heat.

 

**AGE TWENTY. NOVEMBER. NEW HAVEN**

The summer had passed far too quickly for Rory’s liking and before she knew it, she was almost four months into her second year at Yale. Mid November was a bit warmer this year than it usually was, but she wasn’t complaining about it. The leaves were still turning brown and falling from the trees, they crunched underneath her boots as she walked to and from class and she found herself falling in love with Yale in the autumn all over again.

This new school year was bound to be a good one, she thought. She was allowed to take more English classes than she had been in first year, and she was officially on the Yale Daily News as a reporter, and those two things excited her more than anything else. She lived in a new dorm with just Paris, who was typical Paris, but Rory had actually found herself _enjoying_ being around Paris—which was not something she ever thought would happen back in their Chilton days. Paris was intense and mean, but that was what made her endearing even through her affair with Asher Fleming.

The beginning of the year had been hard for Paris once her lover (Rory still felt weird calling him that) had passed, but the passing of Asher Fleming had weirdly enough opened up a new door to Rory—or, rather, had introduced her to a new person. Logan Huntzberger was… well, he was _something._ He was kind of rude and annoying, very privileged and mean to anyone he thought was beneath him, but he was so intriguing, especially with the whole Life and Death Brigade thing.

That trip had been a whirlwind, really, and it’d only made her more interested in Logan as a person.

She was sure that the sheer amount of pep in her step couldn’t even be squashed by the party she was forced to attend at her grandparents place tonight. Connecting with other Yale alumni didn’t sound like such a bad idea. It’d be nice to see who people went on to become after achieving an Ivy League education, after all her Grandfather was her only example and while he was a very fine example, she didn’t want to work in the insurance business like he did.

She’d even managed to convince Jess to tag along after Dean said he couldn’t. Rory wrangled Jess into a suit and tie in hopes of quelling her grandparents anger when they saw him show up with her. Grandma seemed so worried about making sure the party was perfect that she’d only insulted Jess once, and Grandpa had immediately brought Jess to his side so he could show him the bar. He’d even said something about enticing him to apply to Yale.

“What with your SAT scores as high as Rory’s and such tenacity you’d get in no problem!”

Rory watched them with a swell of pride. It’d taken Grandpa a while to come around to Jess, but when he’d realized just how smart he was, he quickly became Jess’ biggest fan.

“Come Rory, lets get ready together,” Grandma said, gesturing up to the staircase.

Rory looked at her funny. “But I already am ready, Grandma.”

“We’ll just freshen up, then!”

 

* * *

 

Rory bounced on the balls of her feet, noticing that there seemed to be _a lot_ of men at this party, and she really didn’t want to talk to any of them. She’d lost track of Jess over an hour ago and it was making her feel rather anxious. Not wanting to deal with any more of her grandfather’s peers and their sons, Rory slipped into his office and picked up the phone to call her mother.

“I told you,” her mother had gloated, which only made Rory feel worse. Their conversation didn’t last very long, but Mom had joked about telling her all the various ways there was to get out of the house if she didn’t want to be auctioned off. They said sad goodbyes, and Lorelai teased that she’d better go find Jess in case Grandma had actually locked him in the basement with plans of murder.

By the time she made it back out, she’d been cornered by a man named Jordan in her search for Jess. She’d come out onto the balcony thinking he might’ve escaped out here, but he was no where to be found. Maybe her mom was right, maybe Grandma _had_ murdered him.

“Rory, there you are,” a familiar voice called out to her, though it wasn’t Jess’. Rory leaned around Jordan to see Logan, and stiffened up once he put his arm around her waist. “I’m late, I’m sorry, don’t be mad.” He said to her and she just stared at him. He turned toward Jordan and smiled in greeting. “Logan Huntzberger.”

“Uh, Jordan Chase.”

They held a small conversation that Rory barely listened to, itching to get out of the grasp of this man bordering on strange and acquaintance. When Jordan left, Logan let her go and apologized, saying he’d only stepped in because she seemed cornered. She thanked him, and held a small conversation in which he seemed to hint that he knew her grandmother personally. She opened her mouth to ask him about it, but her grandfather appeared just then and took over the conversation.

When he left, Logan called out to Finn (who Rory didn’t even know was there), and they made their way to the pool house with Colin in tow only to find Jess there reading on the couch.

“Jess!” Rory cried rushing over to him and leaning over the back of the couch to get a better look at his face. “I’ve been looking for you everywhere!”

He placed his book into his lap and turned to look at her, an apology in his eyes. “I told your grandfather that college really wasn’t my speed and he kind of banished me out here, saying I’d probably feel more comfortable since this is a _Yale alumni event_. He did lend me one of his classics at least.” Jess held the old, pristine copy of _A Tale of Two Cities_ up for her to see.

“I’m so sorry,” Rory said, placing her hand on his shoulder.

Logan cleared his throat behind them and Rory jumped, twisting to find Colin and Finn snickering at her. Jess slowly turned around to face them as well.

“This the boyfriend?” Logan asked, moving in to offer his hand to Jess.

“No, this is Jess. I told you about him at the event, remember?”

“I guess I just assumed Jess was a girl,” Logan said, grinning from ear to ear in a way that made Rory feel a little defensive.

She huffed a bit, crossing her arms over her chest. “Well, he’s not.”

“The girl’s touchy,” Colin joked and Finn smirked.

“I’m not _touchy_ , it’s just that Jess is not a girl. My name is Rory and none of you have made the assumption that I’m a boy.”

Logan laughed. “Well, that’s because we all have eyes, Ace.” He moved in to shake Jess’ hand. “I’m Logan. Logan Huntzberger.”

Jess eyes lit up in recognition at the name and he clasped Logan’s hand from over the couch. “I’ve heard of you.”

“Yeah? Only good things I hope,” Logan said, throwing Rory a grin and she blushed without meaning to.

Jess shrugged a bit, standing up from the couch to stretch and face everyone properly.

“Well, we’re probably just going to chill out in here. Maybe get a little drunk. You’re welcome to join us, of course. We aren’t an exclusive group all the time.”

Jess narrowed his eyes at Logan and Rory could feel the tension building between them.

“Jess and I aren’t big partiers,” she tried to explain, and Logan just shrugged.

“Suit yourself,” he said, then turned back to Colin and Finn. “Let the hunt for booze begin, boys!”

Things got a bit rowdy and out of control rather quickly, and Jess left the pool house for fresh air and quiet. Finn and Colin booed after him as he left and Logan laughed, hands spread out wide when Rory glared at them.

“You know this isn’t your house, right?” She asked.

“It’s not yours either,” Logan retorted, raising his third glass of scotch up to the ceiling lights.

Rory rolled her eyes, but she wasn’t annoyed enough to stop them from disrespecting her grandparents house. She kind of hated to admit it, but she was actually having fun with these guys. The only problem was Jess, really. When he came back, he came back looking more annoyed and anxious than when he'd left.

“Dean’s out front,” he said after she gave him a weird look, curious as to why his energy seemed more upset than before. “Says he came to surprise you. He’s not happy I’m here.”

Rory felt the pressure of everyone’s eyes on her and she shifted on the couch, smoothing out her dress and fixing her tiara. She pushed herself up with a deep breath and said, “Well, he didn’t want to come originally so he doesn’t get to be mad.”

Jess only shrugged.

“Who is this Dean, exactly?” Finn asked, looking between everyone in the room.

“He’s my boyfriend.”

“Well,” Logan said, standing up and snapping his fingers excitedly, “we gotta see this guy!”

“What?” Rory asked, now feeling the bubbling of anxiety in her stomach. Dean was already mad enough, he didn’t need to be provoked.

“We gotta see the man who won your heart! Make sure he's good enough for you. Lets go, boys!” He said, calling Colin and Finn after him with the wave of his hand as he made a run for the driveway.

“But—Hey!” Rory said, stalking out after them and Jess followed closely on her heels.

When they got to the driveway, Dean was standing there in the same tux he’d worn to prom and Rory felt a wave of nausea but she fought it off, not wanting to think about what’d happened or the way she’d felt that night. Jess stayed far behind, watching with curious eyes and she gave him a small, reassuring smile that he returned to her. Logan, Colin, and Finn stood near the front door, watching in anticipation.

She walked closer to Dean and forced a smile on her face, not entirely ready to face his wrath. “Dean, hi! I’m so sorry. Were you waiting out here long? I didn’t know you were going to come, when we talked about this before you had said you were busy, so I just assumed I wouldn’t see you tonight. I asked Jess to come along because my mother didn’t want to, and she and my grandparents got into a little tiff, but what else is new, right? Anyway, these are some of my friends from Yale. The party was very boring, so we—“

She cut herself off, taking in the angry look on his face, biting her lower lip. _Deflect, deflect, deflect,_ she chanted.

“Is that a new shirt?” She asked, changing the subject out of nowhere, knowing full well his shirt was not new. “Cause, I like it.”

“What am I doing here, Rory?” He asked, voice hard.

Rory shrugged back at him, not knowing what the right answer was. “You’re here to meet Yale Alumni with me? Though turns out it was more of a matching making party than anything else, not that I knew that.”

Dean scoffed. “Great. So, even your grandparents know we’re practically not together anymore.”

“What are you _talking_ about? Of course we’re still together!”

“We hardly ever see each other anymore! You’re only about a half-hour away, but yet I never see you. _He_ sees you more than I do,” Dean spat, gesturing off to Jess violently.

Rory crossed her arms tightly over her chest. “Are you seriously bringing this up again?! I thought I already told you that Jess and I—”

“You let him sleep over at your dorm, Rory! But yet you don’t want me to spend the night!”

“Yeah, because Paris could hear us!”

“You went to his mom’s wedding with him and the whole town talked about how you two were slow dancing and looking _so in love_.”

Rory opened her mouth to argue, wanting to bring up how Avery had been there, and how she invited him to Liz’s wedding and he’d rejected the invitation; she’d invited him here tonight, too, but he had said he didn’t have the time. And yet he was here now and angry with her for bringing Jess instead. How was that fair to her? Of course, she couldn’t get any of these thoughts out because Dean continued on, not letting her get a word in edge-wise, as per usual.

“Every time I turn around you’re with him! You have let me run around here like a damn fool, tripping over myself to make you happy. I have dressed up like this,” he gestured to his tux, “so many times for you so that your grandparents will _approve_ of me. I built you a _car_ , I made you a bracelet. I _loved_ you, but you know what?” He asked, looking up and down, focusing in on her tiara in disgust. “I don’t anymore.”

Rory swallowed hard against the lump in her throat and the tears stinging at the back of her eyes. “Dean—”

“You look nice,” he said, cutting her off coldly as he opened up his car door and got inside. “I’m sure _Jess_ and those other _Yale guys_ appreciate it. Bye, Rory.”

And he drove off then, leaving Rory with nothing but her tears.

 

**AGE TWENTY-THREE. JUNE. PHILADELPHIA**

They’d walked all the way back home in silence.

Jess had _wanted_ to say something, but he didn’t know where to start, and by the time he was ready to try, they’d already made it back to the loft. Jess let Rory get changed in their room as he washed his face and brushed his teeth and then they switched off and by the time Rory made it back into the room, Jess was already in bed though he wasn’t asleep.

“Okay, I’m ready to talk now,” Rory said sitting on her side of the bed.

Jess made sure to let her know that she had his full attention, happy when she caught the drift and opened her mouth to continue.

“I… don’t like that you went to my mom first because it,” she paused, closing her eyes firmly before continuing, “it reminds me of when Logan planned out our whole lives in California and told my mom all about it before he even _thought_ to talk to me. And, when I was eighteen, Dean did something really similar on prom night. He and my mom basically planned my entire loss of virginity together and I didn’t find out until I was already _at_ the hotel.”

“You never told me that,” Jess said. His mind was finally making all the connections that he’d missed before, and he felt less guilty now knowing that this hadn’t been information he was privy to. “You never told me about Dean or Logan.”

“I know,” Rory said, tucking her feet under her thighs. “I just never thought that you would…”

“That I would do that to you, too,” he filled in, nodding once. “I get it now.”

“You do?” Rory asked, looking at him in desperation. There was something behind her eyes that made his stomach clench; she thought she’d been irrational for her reaction, that she didn’t have the right to be angry with him.

He reached out and threaded their fingers together. “Yeah,” he reassured her, hoping to God he sounded genuine because he was, he really, _really_ was, “I do. Your feelings are yours, Rory. You’re allowed to be angry or sad or unhappy, whatever it is you want, and no one should make you feel otherwise. Just because my heart was in the right place—and it was, I promise you that—doesn’t mean you have to accept what I did or forgive me. I’m sorry for what I did, I fully recognize how and why that would upset you.”

She stared at him for a long time, a single tooth poking out over her bottom lip. “That’s exactly why I forgive you,” she whispered, eyes wet now.

He leaned forward and wiped away some of the condensation forming on her lashline. “Don’t cry,” he whispered. “I hate it when you cry. I never know what to do.”

Rory giggled, wiping at her own eyes as well with a cute sniff.  "That's okay." She got up to turn off their overhead light and crawled back to him when their room was completely dark. They intertwined their fingers yet again and Jess stroked the back of her hand, remembering what Avery said about how he had to explore being open and free with Rory to really _know_ if this was what he wanted.

“I’m sorry I didn’t tell you about talking to them,” he whispered to her. “I’m sorry that I talked to them first, too. I was just scared that we would do this and then they’d disapprove and it’d ruin not only us but their marriage as well. We’re interlinked in so many ways, Rory, it’s a little terrifying if we don't actually work out in the end.”

“I know,” Rory agreed, whispering back. She moved in a little closer so that his chin rested atop of her head. “I get it, Jess. I do. We're taking a big risk right now, but ... Thank you for apologizing. That’s something Dean and Logan never once did, even after I told them how upset it made me.”

Jess grunted at that, knowing damn well that neither Dean or Logan were the type of men to apologize. He'd watched them bulldoze right over Rory's feelings too many times. He shifted to place a kiss on the top of her head, trying to let her know how he felt through his actions but he didn't think a single kiss was enough for what he wanted to convey. “I’m not them," he said, finally. "I was trying to be them, a mesh between the two of them or something, I think… but—”

“That’s not what I want, Jess. I don’t want you to be a mesh, I want you to be you. I just want _you_.” She tipped her head back and wiggled out of his arms a bit to look at him. “You’re enough.” A tingle ran down his back at those words, goosebumps forming on his skin. Rory must’ve felt them because she started to caress his arms in soft strokes. “So, Luke says we’re together now?”

Jess laughed. “I don’t think it’s up to Luke if we're together or not.”

“Ding, ding, ding. Right answer,” Rory said, her voice sleepy and slow all of a sudden. Jess pulled her in a little closer. “Hey, I wanted to ask you something...”

“Ask away.”

“What’d my mom say when you talked to her?”

Jess thought back to Lorelai’s words, the way she seemed to disapprove but approve all at once. The way she’d searched for flaws in his craft and asked Luke for a second opinion to see if he were really telling the truth or not. But then he remembered the way she seemed to cave, and the way she questioned why he was asking her for permission after everything he and Rory had been through up until that very moment.

“She didn’t think we needed her permission.”

“Really?” Rory asked, sounding a little surprised. “I expected her to burn the house down with you in it or something. Maybe light your car on fire so you couldn’t make your way back to me.”

Jess chucked and absentmindedly ran his fingers up and down the dip of her spin. “I thought so, too. In the end she said it was about time that we explored this.”

“And... You and Avery are done?”

“Mhm,” Jess nodded. “We’re done.”

“And you want to date me?” It sounded like she still couldn’t quite believe it. There was a sort of childish wonder to her voice that he loved, and he took a deep breath and reminded himself that it was okay to love things openly about her again.

He nodded against her again. “I do.”

“What took you so long to ask? Luke said you went there a month ago.”

“I wanted you to be my date to the gala... I was trying to psych myself up to ask you.”

Rory giggled at that. “Aw, like prom.”

“Not like prom,” Jess denied. “Nothing like prom. I hate prom.”

“So much like prom,” she teased, slipping a leg between his in her plight to get more comfortable.

Jess grumbled in his disagreement, but he let her have it since she wanted it so bad.

“I want to go on a date before that. The gala's not til August, right?" He nodded against her head for the first time, and Rory hummed thoughtfully. "Okay, then we'll definitely go out before then, and I get to pick where and when because you clearly don’t know what you’re doing. You’d think you’ve never dated before.”

“I get stupid when it comes to you,” he confessed, knowing the alcohol was making him a little braver when it came to his emotions tonight. “It’s been a trend for about three years now, probably. But, fine, you pick the time and place and I’ll just show up.”

Rory’s breathing started to deepen and he knew she was close to falling asleep. “Just make sure you look really pretty.”


	7. Chapter 7

**Notes for the Chapter:**

> The past is real angsty right now y'all, and will probably continue to be for the duration of this until the past meets up with the present loool. BUT I may throw in some cute 13-year-old Literati to balance some of the angst of the past out, maybe. But, hey at least they're happy and having good sex in 2008, right?
> 
> As always don't forget to leave a comment because I love feedback!!

**AGE TWENTY. JANUARY. STARS HOLLOW.**

For first time in a long time, Jess Mariano and Rory Gilmore were single at the same time.

The last time this had happened they’d been thirteen and hardly even old enough to date, but now they were both twenty and trying their best to navigate the world all on their own. Rory’s relationship with Dean had lasted almost five years, but it showed in the way that Rory grieved for it. Jess had his suspicions that Rory had been over Dean long before he’d embarrassed her with a public breakup on her grandparents’ driveway, but that didn’t mean she was hurting any less.

“Can you believe he’s in a new relationship already?!” Rory had complained to him one day. “He didn’t even give it time! He’s just walking around town, hand-in-hand with _Lindsay Lister.”_ Her voice got oddly high-pitched whenever she said that name, Jess thought it was both funny and subsequently annoying.

“The guys a jerk, Rory. Breaking up with you in front of everyone like that? Moving on practically the next day? He’s a total jerk.”

Rory didn’t seem satisfied with those words, but they were about the only source of comfort he could offer. He loved his best friend, but he was still primarily focused on his own heartache to really offer the selfless support that Rory wanted from him.

Avery had broken up with him over Thanksgiving. It’d been a mature, mutual parting stemming primarily from issues such as: Avery’s lack of funds to come home often, Jess’ lack of funds to visit UMASS often, and the fact that Avery was starting a whole new part of her life that she deserved to explore freely without worrying about some boy back home. It still stung though. He hadn’t wanted to agree to the break up, but there was no logical reason why they should’ve stayed together.

“We’re not breaking up because we don’t love each other,” Avery had said, trying to comfort herself just as much as him. “I love you, Jess. A lot. But it just doesn’t make sense to stay together right now… maybe when I’m finished college we’ll pick back up again?”

Those words and prospect of finding each other later in life had stuck with him more than he’d like to admit. He didn’t consider himself the super romantic type, but being with Avery for three years had brought forth a new side of himself that he hadn’t even known existed. In fact, Jess had spent _months_ wallowing in silence after the break up, there was a possibility that he’d even been _pining_ , though he was less likely to confess to the latter.

Crying over someone who was gone was no help, he told himself. He had to focus on other things, the same way Avery was focusing on her own shit. But, that was the problem, Jess didn’t _have_ his own shit to focus on. He wasn’t going to college. He wasn’t doing anything but working at Luke’s and he yearned for some type of freedom, so he’d started writing more. It was all jumbled up, personal musings about his feelings about his childhood, his mother, Avery, Stars Hollow and just _his life_ in general. He was sure none of it would make sense to anyone but him, and he had every intention of keeping them private, but things changed thanks to Mr. Ramesh.

“With Avery gone I have no one to hold my creative writing circles with,” he’d said one day in the diner. “Her sister isn’t very artistic. Claire _loves_ art, but her interest is based in the creation of it and the history behind it. My wife and I are certain she’ll wind up working in a museum. We went on vacation back to home to Trinidad and Claire dragged us around to various museums on the island. Never learned so much about my own people and culture.”

Jess smirked. “Sounds like it was a good time.”

“Oh, it was. Exhausting, of course, but good. Have you started writing that novel yet?” Mr. Ramesh asked him, a twinkle in his eye. “I see you’ve been carrying a notebook around with you for the better part of last year. I’d love to read some of your work.”

Jess hadn’t thought it’d be an informative experience, much less a fun one, but Mr. Ramesh still had the same flare for education and self-improvement that Jess had remembered. He felt a little self conscious letting an authority figure who happened to be his ex’s father read his personal musings, but the high he felt when praised was enough to make it all worth it.

“This is remarkable, artistry. If you don’t publish this for the world to see, you’ll be depriving us all of your talents.”

Mr. Ramesh was definitely over-selling it, but Jess didn’t mind. Even at twenty, praise didn’t fall into his lap so easily.

Lane and Rory complimented him on things here and there—his intelligence, his looks, his taste in music and literature, but they’d never read his prose, they didn’t even know he was a writer at all. And that wasn’t their fault, either. Jess had long made the decision to keep his writing separate from his friends. He knew that Rory, especially, would want to read it and talk about it at length. She’d gush and tell him how great it all was, but Jess had a hard time believing in Rory’s subjectivity when it came to him.

He’d decided that he’d only show her _when_ and _if_ he got published one day.

 

**AGE TWENTY-THREE. JUNE. PHILADELPHIA**

“You gonna tell me where we’re going?”

Rory shook her head with a smile. “Nuh-uh. It’s a surprise.”

It was a hot, June day, and Jess felt like he was dying as they walked the streets of Philly. Rory had demanded he meet her at the Metro office so that they could walk to their destination as it was closer to her place of work than it was to their apartment. There was a part of him that regretted allowing Rory to choose the venue for their first date. If it’d been up to him, they’d have went to a book store near their house, grabbed a couple of drinks and then went home for sex. It was fool proof, but Rory had always been a bigger romantic than he was.

And, besides, he wasn’t sure if sex on the first date was something Rory even _did._

He was trying not to be presumptuous anymore, but he also didn’t want to leap into this head first and wind up dazed and confused when she rebuked his advances. It was better to just read her body language, see what she wanted. He knew they’d had their trysts in the past few months, and while they could’ve been used as proof that sex was a-okay, Jess still didn’t want to make any sudden movements.

Rory had linked their fingers together as they walked, leaning into his side in a way that said she didn’t mind him being in her personal space, and despite the heat, Jess really didn’t mind either. They chatted about nothing and everything on their way to Rory’s secret destination. They made it onto South Street and passed one of Chris’ favourite restaurants in the area, _Caribbean Delight_ , walked up another block and stopped right in front of the Magic Garden.

“Ta-da!” Rory said, sounding proud of herself.

Jess laughed and squeezed her hand. “I’ve actually never been inside before, to be honest with you. So, good pick.”

“I know, I asked Matt and Chris before purchasing the tickets..”

“How very prudent of you.”

“That’s me, Miss Prudent!” Rory chimed, turning to face him with a big grin. She leaned up on her toes to kiss him and he tingled all over. He cupped her cheek and pressed in a little harder, but she giggled and pushed him away. “People are staring.”

“So?” He asked, leaning in again to kiss her. “I can’t get enough.”

When he broke away, Rory was blushing scarlet and Jess smirked.

“Come on!” She said, dragging him toward the gate. “I want to do the outdoor labyrinth first.”

They explored the outdoor mosaic, taking their time to really _look_ at everything in sight, or at least as much as they could process. Isaiah Zagar was an incredible artist in Jess’ eyes. His dedication to the gardens was absolutely phenomenal, and Jess yearned for the day when he could be as dedicating to his writing as Zagar was to this masterpiece.

There was a sort of romanticism about this place that made it perfect for a first date. It all felt so closed in and a little claustrophobic, especially in the indoor galleries, but the tighter spaces kept him rather close to Rory, his front pressed up against her back. He did all he could to keep himself under control, when she pressed her ass purposefully against his crotch. He looked down to glare at her, but she acted like she didn’t know what she did wrong or something she ignored his look all together.

“Wasn’t that amazing?” Rory gushed once they’d left.

Jess didn’t know how long they’d spent there, but it felt a bit like a time warp. They’d explored so many things, took in so many exhibitions and talked with some of the tour guides and exhibition workers when they were free. Rory had learned about the _Garden Sips_ event that took place on every Wednesday at the beginning of the month from May until September and she was really quite determined to come back and Jess didn’t mind.

“It was,” he agreed, slipping his hand back into hers.

She smiled up at him. “Wanna go out for a drink before going home?”

“Are you going to leave your car at the office?” He asked. “Because it won’t be fun if only one of us can drink.”

“No, lets drive it home and then go out. The fun should not stop here… Unless you want it to, in which case I totally respect that. Do you want it to?”

Jess smiled at her babbling and brought her hand up to his mouth to kiss it. “Nah. I can go all night.” He winked and Rory turned red, but she didn’t shy away.

“Yeah, well, _you’d better.”_

 

**AGE TWENTY. FEBRUARY. STARS HOLLOW.**

“So, you and Huntzberger got caught trying to fuck at your Grandparents vow renewal, huh?” Jess asked, teasing smirk in place. “And here I thought you didn’t like him very much.”

Rory blushed, scratching at her chin as she averted her gaze from his. “Well, as it turns out he annoyed me because I… _like_ him,” she admitted, sounding pained to do it. “Or, at least I’m attracted to him.”

“How very middle school of you.”

“Shut up!” Rory said, finally looking at him then, eyes filled with embarrassment.

Jess shrugged, holding his hands up in defeat. “Sorry.”

She softened in her seat on the couch, licking her lips a little self-consciously. Jess wondered what she was thinking about and if she were really that embarrassed to be attracted to Huntzberger. He was proud of her for moving on, really. Dean had been a real piece of work and Rory deserved someone better. He wasn’t sure if he’d say Logan Huntzberger _was_ better per se, but he seemed like a step in the right direction, and at the very least he’d be a good rebound fuck.

“How are you holding up?” Rory asked, pulling Jess out of his thoughts.

He shrugged a bit. “What do you mean?”

“Jess,” Rory chided, imploring him to tell her the truth. “Come on.”

He folded his hands behind his head and leaned back into the worn cushions of her living room couch. “Honestly, Rory? I’m fine. Avery and I broke up in _November_ , it’s now February. I’m just fine.”

“You haven’t dated anyone since.”

“So?”

Rory shrugged a little. “I’m dating after Dean and you’re not… I just thought that you’d be the one to date someone else first.”

“I like to live on the edge. I’m very unpredictable.”

She rolled her eyes at him and he smirked at her just before she hit him in the chest. “Jess, I’m serious. Are you sure you’re okay?”

“Just dandy.”

Rory sighed in defeat and Jess felt a little guilty, but he didn’t want to deal with this shit. Was he over Avery? No, not in the slightest. The break up had gut him, but honestly? Who cared? It wasn’t something he wanted to talk about, especially not with Rory. He was happy for her and the way things were going with her, he didn’t need to rant about his own problems and make her feel guilty. Jess knew if Rory got wind that Jess was unhappy and wallowing then she’d judge herself, hold herself up to his standard because that’s the way Rory Gilmore was.

She was being free, living life and that was a _good_ thing.

“Okay… But only if you’re sure?”

“Completely,” he lied.

 

**AGE TWENTY-THREE. JUNE. PHILADELPHIA**

They chose to sit in the dining room side of the sports bar they’d stumbled into after parking Rory’s car in the underground garage. It wasn’t exactly _romantic_ but Rory knew this place had really good ribs and she was craving some. Neither of them paid any real attention to the game on the screen, choosing to focus on their food and each other. Rory couldn’t help but notice that Jess looked really, really happy and that only made her feel happy, too.

This date had been amazing so far. Jess had enjoyed the Magic Garden, though he wasn’t as open about it as she was, but she could tell. He’d wrapped his arms around her from behind as they stared at the artwork surrounding them taking it all in to the best of their ability. He’d moved her hair to the side to kiss at her neck and lightly suck on her pulse point and she’d felt as if her skin were on fire. Rory wasn’t quite sure how he managed to get these reactions out of her without doing much of anything at all, but she wasn’t really complaining.

She stared at him from across the table with a smile, raising her leg to brush his leg with her foot. He raised an eyebrow at her and she pulled her foot back, toeing her shoe off so she could explore him with the pads of her feet. She slipped a bit in her chair as she made her way up his leg to his crotch, grinning like she struck gold when she came into contact with his crotch. She didn’t really know what she was doing, but the desire to touch him had been building since they’d been in the Magic Garden.

“Rory,” Jess growled, leaning a little closer to her.

“Yes?” She asked innocently, rubbing him a little harder and enjoying the way he seemed to grow under her touch. God, what was it about him that turned her into this person?

His eyes fluttered closed and it looked _so good_ in the clandestine light of the bar. “You’re trying to kill me, aren’t you?”

“Absolutely not.” Rory pouted, but she didn’t let up on arousing him, in fact she put more pressure on him and enjoyed the way his throat hollowed with a sharp in-take of breath. “You promised me _all night.”_

Finally, he grabbed her foot and removed it from his lap, but she liked the way he looked pained at the action. “You’re going to have to stop teasing me if you want me to last that long.”

She grinned, slipping her foot back into her shoe. “Okay, okay. I’ll be good.”

 

**AGE TWENTY. MARCH. STARS HOLLOW.**

Miraculously, Jess felt a lot better come March.

There wasn’t such a heavy weight on his chest and hanging out with Mr. Ramesh actually _helped_ to get over Avery. A lot of his personal musings were about her, and he was sure Mr. Ramesh knew, but thankfully he never brought it up. Their sessions brought Jess peace of mind while also forcing him to confront things that he’d never allowed himself to linger on for too long, like his feelings for Rory Gilmore.

He hated poetry, but Mr. Ramesh had asked him to read Pablo Neruda’s _100 Sonnets_ for their next discussion, so it’d found a home in his back pocket this past week. At first the poems had caused his mind to wander to Avery and their old intimate relationship. He still missed her desperately; missed the way she’d ride him, the soft feeling of her moisturized hands on his skin, and the way she kissed him hot and dirty, tugging his lower lip between her teeth. He missed the way she’d curl up into him after a few rounds of sex, and the silky feeling of her curls in his finger tips, but as the days went by, his imagination began to shift.

Neruda was all about longing and desire, and while Avery still held an important part in his heart and his mind, he’d made his way into longing for someone he never thought he’d long for again. At some point in his life Jess had harboured a crush on his best friend, but he’d squashed it the moment he’d fallen in love with someone else. Unfortunately for him, Rory was beautiful, smart, and elegant; that hadn’t changed just because he’d had another woman in his life. He admired Rory’s beauty from afar sometimes; she had this serene-like quality to her that made her look dreamy and surreal. She almost seemed blurry at the edges, like if he reached out and touched her he’d slip right through. Maybe that was why he sought such a physical—yet platonic—relationship with her.

“Y’know, for a man whose constantly droning on with anti-education rhetoric, you’re certainly here a lot,” he remembered Paris saying to him one night. “Sleeping on our couch, helping us buy groceries, walking Rory to and from class… If I didn’t know better I’d think you were finally thinking about post secondary education.”

Jess just grabbed a handful of popcorn and threw a couple in his mouth instead of answering.

“Or maybe he’s just here _for_ Gilmore,” Doyle filled in, nudging Paris a bit with a wink.

“Very insightful of you, Doyle.” Paris leaned forward to look at Jess a little closer. “You in love with Gilmore, Mariano?”

He snorted. “Yes,” he said sarcastically, “that’s _exactly_ it. I’m in love with Rory, you’ve figured out my big secret.”

Rory came back in with the pizza just before Paris or Doyle could rib on him a little more, and he remembered feeling a huge sense of relief.

He hadn’t thought either of them had a point at the time, but now he was starting to wonder if he _did_ have ulterior motives, ones that he didn’t even know about. The resurgence of old attraction aside, Jess couldn’t be sure that he even knew what he felt. Did he have feelings for Rory Gilmore? Was it worth having a talk to her about when she'd just broken up with Dean? There was a real chance that talking about this could mess things up, and Jess wasn’t about to cross that line.

Jess sighed, trying to ground himself back into the current moment. _100 Sonnets_ was open in front of him and flipped to the next page—

 

 

> _I love you as certain dark things are to be loved,_
> 
> _in secret, between the shadow and the soul._

Jess clutched the book a little harder, sinking his teeth into his flesh.

 ****

**AGE TWENTY-THREE. JUNE. PHILADELPHIA**

By the time they left the bar, Rory was feeling high and bubbly due to all the wine she’d ordered. She swayed in the street, dancing to music that definitely wasn’t playing anywhere but in her head and she grabbed Jess by the hand and made him join her, though he refused to humour her.

She stumbled into him when she’d started spinning, locking her arms around his shoulders as she pushed up to kiss him. “You’re so pretty,” she whispered and he laughed good naturedly. “I can’t wait to see you without your clothes on.”

Jess snorted. “Wow. Are you just using me for my body, Gilmore? I knew that’s all you wanted.” He was just as drunk as she was if the flush on his cheeks was anything to go by.

“Noooo,” she drawled, feeling oddly serious as she looked at him. “I love you.”

His hands tightened on her waist and she relished in the feeling. “You love me?”

She nodded. “I love you _so much_.” He opened his mouth to say something, but she put her finger to his lip. “No, shhh. Don’t say it back, or don’t say whatever it is you were gonna say if you weren’t going to say it back. I just wanted you to know that I do. That I always have. I don’t want anything to ruin this night, I just wanted to say it.”

“Okay,” he said, brushing some hair away from her face. She loved the way he said ‘okay’.

Rory twisted out of his hold and grabbed him by the hand, dragging him off to their apartment. “I’m going to do so many things to you tonight, you won’t even know what to do with yourself.”

“Oh really?” He asked her, laughing a bit as they entered the lobby and received an odd look from concierge but they both ignored it.

“Yep!” She said, popping the ‘p’ loudly.

She was all over him when they got into the elevator, her hands running down his chest and her lips attacking him in a messy, drunk way. Luckily, no one came with them, but even if they had, Rory isn’t sure that would’ve stopped her. She groaned unhappily when the elevator doors opened to their floor and Jess dragged her off.

 

**AGE TWENTY. APRIL. YALE**

Jess wanted to support Rory’s budding relationship with Logan, but there were a lot of red flags already.

For one, Logan told Rory he didn’t want to be exclusive, but then when she’d shown up to a costume party with his friend Robert, Logan had the nerve to get jealous. Two, Logan didn’t call Rory to make plans, not that Jess had ever been good at that either—Avery had handled most of the planning in their relationship, but Logan’s lack of initiative seemed to upset Rory to the point of getting drunk and crying on the bathroom floor. And, three, Logan had a tendency to bulldoze right over Rory’s feelings whenever she was trying to explain her unhappiness about the things he’d done or said.

All in all, Logan Huntzberger sounded like a dick, and Jess thought Rory could _definitely_ do better.

“That guy is stringing you along,” Jess explained to her, laying down on her couch, knees up and book in hand. “He doesn’t want to be in a relationship with you, but he doesn’t want _you_ to be in a relationship with anyone else. He wants you sitting at home waiting for him while he goes off and fucks whoever else.”

Rory had opened her mouth to disagree but her brow crinkled once she realized he was right and she quickly pursed her lips.

“I don’t say this to hurt you. I know you like him…” He trailed off and thought of the best way to word what he wanted to say next. “I just think you might like him more than he likes you. Happens to the best of us.”

Again, Rory didn’t say anything. Instead, she got up and stalked into her room, her bag slung across her shoulder when she emerged and announced that she needed to get to class a little early to talk to her professor. Jess hadn’t bothered to point out about how she’d once complained that this professor was always late and therefore he probably wouldn’t even be there before her, knowing it was better to just let her go.

When she returned a few hours later she had a huge smile on her face that reflected in her eyes.

“I went to talk to Logan,” she said, sitting next to him still beaming.

Jess sighed, practically knowing what was coming next. “Yeah, and?” He didn’t put down his book.

“He’s agreed to be my boyfriend.”

“ _Great.”_ How could she be so naive?

“What?” She asked, eyebrows drawn together. “You said he was stringing me along, and now he’s not. We’re going to be together for real now and I’m excited about it.”

“Yep,” he said, voice airy, light, and _very_ sarcastic. “Sounds real exciting and not a bad idea at all.”

Rory grabbed his book from his hands and slammed it shut. “ _What_ is your problem?”

He stared at her blankly. “I don’t have a problem.”

“Yes, you do. You’re giving me attitude. I don’t see the problem, Jess.”Her voice was getting weirdly high pitched in that way it did when she was angry with him. “Logan is nice and handsome, and oh _he likes me_ , did I mention that because I think I might’ve forgotten. So, tell me, Jess, how is me being with Logan a _bad idea?_ He _likes_ me, Jess!”

Jess rolled his eyes. “Anyone ever tell you that you have tunnel vision?”

She bristled, nostril’s flaring. “Only you right now.”

“Huh.”

“Jess!”

“What, Rory?! I already _told you_ what guys like Logan are like, but you’ve decided that you want to be in a relationship with him so go ahead.”

There was a more rational part of his mind that questioned his own anger. Just a few months ago, he’d been gunning for Rory and Logan, but there had been a part of him that hoped they’d only be a fling. Logan was _technically_ a rebound from Dean, and rebounds weren’t supposed to become full-fledged romantic partners. Rebounds were supposed to be fun for a time, and then you got over them and realized that there was someone better for you—more suitable. Someone who had the same interests, read the same books, was there for her in her darkest times. Not some rich boy who didn’t understand a thing about her and wanted her at home waiting by the phone at all times and would put up with his shitty treatment.

Rory nodded then, stiff and jerky. “I see what this is. You’re jealous,” she said like it was fact. “You’re jealous because I’m with someone sweet who likes me and you’re single, alone and bitter.”

“ _Wooooow_ , you should be a _detective!_ Maybe join that legendary mouse?”

She blushed, but didn’t let him win; in a way, he was a little impressed. “You said you were fine after Avery, well you’re not fine, obviously. The Jess I knew before would’ve been happy for me. But this new Jess is so washed up and sad over _some girl_ that he’s gotta take it out on his best friend.”

“You know what? Fuck you, Rory.” He got up from the couch and grabbed his bag from the table, looking around her dorm for any of his scattered items. “You want to be stupid and date a guy whose going to lie to you, probably cheat on you, and continuously bulldoze over your feelings? Go right ahead. I don’t give a single fuck.”

“You don’t know that he’ll do that! You don’t know anything about him!”

Jess rolled his eyes and grabbed his book from the couch, stuffing it into his bag before wandering off into the bathroom to grab his toothbrush and hair products. He took a deep breath and did one extra scan and turned on his heel to leave only to find Rory in the doorway with misty eyes.

“No,” he demanded, pointing at her. “You don’t get to fucking cry and manipulate me.”

“I’m not manipulating you!” Her bottom lip trembled. “I just thought you’d be happy for me!”

“If you want blind, unconditional support for your extremely _stupid_ decisions, then talk to Lane, not me. She’s your soft-hearted friend who will never point out your wrong doings, but I am the friend who will always tell you the truth. Now, get out of my way.”

Rory shook her head him. “No.”

“Rory, _move_.”

“No!” Her voice cracked on the word and Jess felt his resolve fading. “I don’t want you to go. I don’t want to fight.”

“This is ridiculous.” Jess studied her before shaking his head. “You think you can just say whatever you want and think I’ll put up with it. Let me go, Rory.”

“I didn’t say anything. You started this!”

“You called Avery _some girl_ , Rory. She wasn’t _some girl_ , she was my girlfriend for three-fucking-years. Is Dean just _some guy_ to you now that you’re fucking someone else?”

Rory shrank under his gaze, she clasped her elbow in his hand. “Well, no…”

“Didn’t think so.”

The gap between the door and Rory’s shrunken frame was large enough for Jess to squeeze through, so he barrelled right past her to check for any more missing items. When he didn’t see any, he fixed his bag to his shoulder and made his way for the door, almost completely knocked back just as Paris entered. He paused for a moment, wondering if it was better to storm out now, but Paris’ intense gaze kept him locked in place.

Her eyes flitted from Jess to Rory and back and then she huffed, crossed her arms over her chest and leaned against the door to close it. “Why are you two fighting?” The hard look on her face demanded an answer.

“I was just leaving.”

“That wasn’t the question, Bukowski,” Paris snapped, and Jess almost flinched.

Rory sniffed behind him, showing up in his peripheral and she wiped at her eyes. “It’s nothing, Paris.”

“Like hell it is! You’re crying like goddamn Snow White and this asshole is standing here like he wants to bolt. Something happened. Now, tell me what or no one’s getting out of here tonight.”

Jess refused to look at Rory so he glanced down at his socks before he reluctantly answered. “We got into a fight about Logan.” God, that sounded so stupid to say. How was this asshole getting in between them already?

“Huntzberger? Why are you fighting over that whorehound?”

“He is not a whorehound!” Rory cried, and Jess looked at Paris with his eyebrows raised like, _This is why_.

“Ah,” she said easily, finally moving away from the door, but Jess let his bag drop to the ground. “Delusion.”

“They’re going steady now,” Jess filled her in sarcastically.

Paris snorted, throwing Rory a look of disbelief. “You really think he can be faithful? And even if he can, you’re going to go with the man who can make you so upset you get drunk and cry on the bathroom floor? God help you.”

Rory shrugged a bit, no longer crying but her face was still red and blotchy. “Innocent until proven guilty, and we weren’t exclusive then. It was a simple communication problem. He said he wants to try and be a good boyfriend to me, that it’s something new for him but he likes me. I’m going to give him the benefit of the doubt.”

“Oh, how _fair_ of you,” Paris said sarcastically, strolling into the kitchen in search of food. “I did warn you about him, Rory, but… Congrats on tying Huntzberger down, I guess.”

“Can no one just be genuinely happy for me?!” She asked desperately, and Jess thought she was about to start crying again. “This is what I wanted! I wanted to be with Logan, and now I am. So, you know what?” She made her way toward the front door to grab her coat and shoes, “You two just stay here, I’ll go. I’m sure you guys could use some alone time to trash talk me and my new relationship.”

“Rory—“

She didn’t give Jess the chance to say any more as she was out of the dorm faster than he could formulate another sentence.

He groaned, bending to grab his bag. “I’m going to head out, too,” he said, turning to look at Paris. “I need to be getting back so that I can help Luke open up tomorrow morning.”

“Okay,” Paris said, shrugging. “I’ll let you know if an intervention is in order.”

He smirked, but he felt a little sad about the way things just went down. “I’ll keep my phone charged.”

 

**AGE TWENTY-THREE. JUNE. PHILADELPHIA**

When they got in, Chris and Matt weren’t home and Rory was sure it was the best a hundred bucks she’d ever spent. She and Jess hadn’t even made it to the bed for the first round. Rory chucked her purse and leftovers into the corner by the door and immediately started working to take Jess’ clothes off. She’d waited for this for too long to wait anymore. Her head was still fuzzy from the wine, but that just made everything more fun.

There was a trail of clothing from the doorway to the couch where they’d collapsed half-naked. Jess had on nothing but his boxers now and Rory stood in her pencil skirt and bra.

“Now that is a look,” Jess said, looking up at her as she straddled him. He stroked her thighs and found the zipper on the back as Rory unhooked her bra and threw it off just before leaning onto him to kiss him again, all teeth and tongue. She ground herself against him, groaning at the delicious friction. It reminded her of when she’d gotten off against his leg and she rubbed herself down harder at the memory, moaning louder as his hands found her breasts and tweaked her nipples. She panted against his chest before pushing herself back up to give him better access.

Jess stared at her breasts in his hands and gave them a firm squeeze which Rory moaned appreciatively at. “Perfect,” he complimented, squeezing them again before he pushed himself up on his elbows to take a nipple into her mouth. She let her head fall back, her hair tickling her hips as he went to work. Rory threaded her nimble fingers through his hair and held him to his chest, not wanting the feeling to end. He swirled his tongue around her areola and then bit down on her nipple softly, sucked it into his mouth and let it go with a loud _pop!_

“Jess,” she moaned, starting to grind against him again and he moaned, switching to her other breast to continue his ministrations. “That feels so good,” she encouraged, now stroking his hair and brushing his bangs back from his face.

He pushed himself up further until he was sitting upright and she was in his lap right before he laid her down on her back and took off her skirt in one swift movement. Jess paused for a moment, staring at her and she felt herself blush.

“No underwear?”

Rory shrugged, biting on her index finger. “I didn’t know how this night was gonna go or where we’d wind up doing it.”

He growled, hovering over her with his hands place on either side of her head. “You’re gonna kill me,” he said just before capturing her lips in a searing kiss.

Rory wrapped a leg around his hips and pressed herself up and into his erection, mewling into his mouth. Their kiss was wet and dirty, leaving her mouth feeling damp when they broke off. Jess sucked his way down her body, focusing on her breasts again for a moment before dipping down to her bellybutton and then he grabbed her hips a little roughly and spread her open wide, one leg hanging over the back of the couch and the other hanging off the edge.

The cool air felt good on her center considering how hot she felt, but Jess’ tongue felt even better. She found purchase once again in his hair and pulled him into her as he licked his way up her whole slit before taking her clit in her mouth with the most perfect pressure that made her keen and bit her lip.

“Oh, god,” she panted, her eyes rolling back into her head as his tongue entered her slowly, made its way back out and entered her again. He kept at that pace, only stopping when she whined at him. “Jess, more.”

He pulled back and looked up at her, his hair a mess and his mouth wet with her juices. “What do you want, Rory?”

“What do you mean?” she asked, feeling dazed.

“Tell me exactly what you want me to do.”

She blushed, unsure of why considering he’d already been face deep in her most intimate place. “I… I don’t know.”

“I think you do. I want you to guide me, okay?”

Rory licked her bottom lip and then said, “I want you to finger me and lick my clit at the same time.”

“Okay,” he said, grinning and immediately went back to work.

 

**AGE TWENTY. APRIL. STARS HOLLOW.**

Jess missed Rory.

It’d been at least two days since their big fight and he was starting to regret some of the things he’d said. Lane had been there to listen, but she judged him for being so harsh. He hadn’t even bothered to argue back, he knew was wrong. It really hadn’t been his intention to hurt Rory’s feelings but he just thought that Logan was a bad idea. Then again, as Lane had very helpfully pointed out, this wasn’t any of his business. Rory’s relationship with Logan was _her_ relationship, and he had no say in whether Rory should be happy about it or not.

“Maybe Rory was right?” Lane asked, eyebrows raised but voice a little timid as if she seemed scared of offending him. “Maybe you _are_ jealous?”

“Oh, you have got to be kidding me.” He rolled his eyes. “I’m not _jealous_ that Rory’s got someone and I don’t.”

“That’s not entirely what I’m getting at.”

He raised a single brow. “Then what?”

“Maybe you’re jealous… of _Logan_.”

“Excuse me?” He asked, voice dangerously low.

Lane shrugged a bit, but she didn’t look apologetic in the slightest. “Rory might be blind to the way you feel about her, but I most certainly am not.”

“I don’t feel any way about Rory. At least, not the way you’re implying.”

“Okay, so all those touches and kisses on the cheek and the forehead, that’s just you being _friendly_ , right?”

“Rory and I have always been like that!” He defended.

Lane leaned forward on the diner table. “And you don’t derive _any_ satisfaction from it at all?”

Jess looked out the window, desperate for a new topic. He really had done his best to turn his feelings for Rory into platonic ones but there was a little thirteen-year-old version of himself running amok in his head screaming differently. Thirteen-year-old Jess didn’t know about Avery and how much twenty-year-old Jess loved her; thirteen-year-old Jess was selfish and liked to barricade himself into his heart and stir up old feelings that Jess was long, long over.

“Mm,” Lane hummed, sounding vindicated at his silence. “That’s what I thought.”

He scrubbed a hand through his hair, scratching hard at his scalp until he felt it start to throb. “I can’t talk about this.”

“Jess,” Lane said a little sadly, and he hated it. He didn’t want the pity. “Rory _loves_ you.”

“No, she doesn’t,” he retorted without thinking much about Lane’s meaning or _what_ type of love she was referring to. Hadn’t he just said he didn’t want to talk about this? “And even if she did, she chose Logan. I’m fine with that.”

Lane let her head fall to the side. “Really?” She asked incredulously. “You’re _fine_ with that? Is that why you freaked out and got into a huge fight?”

“I didn’t _freak out_. We fought because Logan treats her like shit.”

“And you’re frustrated because you wouldn’t treat her like shit, right?”

He ran his tongue over his bottom teeth. “I wouldn’t.”

Lane smiled at him. “You should talk to her about this. Tell her how you’re feeling? It might change things.”

“Or it might not. Maybe it’ll make things worse.”

“You won’t know until you try?”

He bit the inside of his lip.

“You want me to put in a good word for you?”

“I can’t stop you.”

Lane stood up, patting him on the shoulder. “I’ll see what I can do, Bub.”

 

**AGE TWENTY-THREE. JUNE. PHILADELPHIA**

Their second round happened on the way to the bedroom, as Rory felt she’d been more comfortable having sex in a bed rather than anywhere else in their apartment, but they hadn’t quite made it there.

The couch had been all about Rory. She’d come more than three times from being eaten out and fingered alone, and she felt bad that she hadn’t taken care of Jess yet. She pushed him up against the wall just outside their bedroom door and finally took off his boxers, grasping his weight in her hand. His skin was silky smooth and he was leaking with pre-cum, though his boxers had caught most of it. She made a show of licking her hand before taking him in her grasp again and Jess bucked into her hand.

Rory grinned at his reaction, stroking him slowly up and down. She enjoyed the way his hips snapped forward, she liked that she had this much power over him. Finally, she got down on her knees and came face to face with him. There was an uncontrollable fire between her legs, so she squeezed her thighs together to fight against the idea of shoving him into her right there and there.

“Rory,”

“Shh,” she said, looking up at him as she grasped him yet again and pulled him toward her mouth. She let her hand cup the base of his shaft and focused her mouth on the tip. He tasted sweet and she found herself enjoying the act more than she usually did. He groaned when she swirled her tongue around the tip of him and grabbed the back of her neck to hold her still.

“Can you go deeper?” He asked, and Rory looked up at him in affirmation.

She relaxed her tongue, removing her hand from the base of him, and moaned as he pushed in a little further. Deep-throating was kind of something she’d always thought she’d been made for. The Gilmore Girl’s didn’t really have a gag reflex considering how much food they ate on a daily basis, and though it seemed crude, Rory kind of thought her life style had been training her for this moment.

“Do you mind if I take control?”

Rory didn’t want to move out of fear of biting him or suffocating, so she just took a deep breath and gave him the same look as before. Thankfully, Jess understood. He moved slowly at first, his cock slipping in and out in an easy motion. She watched his face and quickly found that she loved the way his brow crumpled and folded in his pleasure, his face twisted to convey his silent torture. He hissed just before picking up speed, but she was prepared for it and tightened her hold a little by pressing her tongue up against the underside of him and hollowing out her cheeks, making sure to keep breathing through her nose.

Jess really seemed to like that as he groans got desperate and his movements started to match. She felt him twitch in her mouth and he pushed her back from him quickly with an, “ _Oh_ , _fuuuuck,_ ” and he came all over her chest and the floor. Rory squeezed her thighs together again, swallowing a moan as she looked at the mess he’d made.

Rory pushed herself up and leaned in to kiss him with a coy smirk. “So, you’re definitely a blowjob kind of guy.”

Jess leaned back against the wall, chest heaving as he tried to catch his breath. “I think you’ve ruined me,” he panted.

“Good,” she said, grinning in glee. “No other woman can have you once I’m done with you. Now, I’m going to get paper towel and clean this up,” Rory kissed him again, this time a little deeper to let him know she wasn’t done with him yet. “Go into the room and rest, I’ll be there soon.”

 

**AGE TWENTY. APRIL. STARS HOLLOW.**

Rory didn’t speak to Jess again until early May right after her first day at her internship with Mitchum. She’d been getting the handle on her work duties, finally getting to the point of feeling comfortable, and she was proud of herself for making it this far. She hadn’t had the chance to gush to anyone about it save for Lane, Paris, Logan, and her mom, but that really didn’t feel like enough. There were plenty of times where she’d picked up the phone to call Jess and tell him all about it, but she just _couldn’t._ His anger about her new relationship with Logan had really hurt her. She wasn’t expecting him to jump up for joy or anything, but she also hadn’t expected him to treat her like a fool for falling for someone he didn’t like.

Lane kept trying to talk to her about the situation, but Rory changed the topic every single time before they could really get into it. She could tell from the look on Lane’s face that she was going to try and get Rory to forgive Jess, and Rory just hadn’t been ready for that, honestly.

She’d been thinking about it a lot, though. She’d been trying to dissect her reason for _why_ she wanted Jess’ approval so badly. In a way, she supposed it went back to her attraction to him, that uncontrollable desire that unfurled in the pit of her stomach every time she so much as looked at him or touched him. It was pathetic, really, to yearn after your best friend like that. She’d figured that if he’d reacted well to her new relationship then she could put all of this behind her and move on, but he’d reacted in a way that made her question if _maybe_ , just _maybe_ he felt the same way about her.

He’d even called her ethereal last summer, though that hadn’t gone anywhere.

She knew they were both getting over their exes and she’d been stupid to have expected him to pursue her the _moment_ Avery was out of his life, but she had, she had expected it and when it didn’t happen she wound up focusing on Logan instead. Maybe that was selfish, to not give Jess the time to get over Avery and pursue her at his own speed, but there was a part of her that just kept screaming, _HE DOESN’T FEEL THAT WAY ABOUT YOU!!_ And she had no reason to believe otherwise.

In the end, she’d found herself reaching out, unable to take the radio silence any longer. She didn’t think she was in the wrong, but she knew she had said something to hurt him and she needed to apologize for that. They’d agreed to meet at a neutral place, a cute little cafe between Stars Hollow and Yale. He was already there when she arrived, reading the table as per usual. Her heart thumped when she saw him, taking a seat across from him with a smile.

“Hey,” she said, feeling kind of awkward. Rory toyed with the ends of her scarf, twirling it around her index finger.

Jess put his book down and Rory took a peak at it. _Twenty Love Poems and a Song of Despair_. She blushed and looked down at her hands, she hadn’t even known that Jess was into poetry, he’d always complained about it but maybe someone had the power to change his mind.

“Hey.”

“How’ve you been?”

“Okay. You?”

Rory looked up at him, blushing a little his gaze. “I’m good… I, I don’t know if you heard but I got an internship. It’s not much but I shadow Mitchum Huntzberger around, get him coffee, take notes, etcetera. It’s cool to be a real newspaper woman, even if I’m just a glorified secretary for now.”

Jess nodded. “Definitely sounds cool.”

“Yeah,” she said, still fiddling with her scarf; her hands were starting to feel clammy. “It is.”

They were silent for a few seconds and Rory found herself looking around the tiny little cafe. It was cute in here, kind of reminded her of Weston’s. She wondered if their pie was half as good. When she turned back to Jess she found that he hadn’t looked away from her and his gaze was just as intense. Rory cleared her throat and rubbed her hands against her thighs.

“So…” She started, not knowing what else to say. The truth would probably suffice. “I, uh… I’ve been thinking…”

“Yeah? That why you asked me to come out here?”

Rory nodded, trying to not to word vomit, she wanted to do this right. “I… I realized that I thought I liked you, as more than a friend, but I know that I was wrong now. Back when I was with Dean, you understood me more than him. You really _got_ me, Jess. You still do but… I think I knew my relationship with Dean was deteriorating so I used you as an escape in my head. You were absolutely the perfect boy for me, I thought… and you being with Avery and therefore out of reach just made you all the more desirable to me.”

His face was starting to shift as she explained, and she could see the anxiety building and the panic starting so she rushed to finish before he got up and bolted.

“But, now, that I’m with Logan, I’ve realized that my feelings for you were based on wanting to date someone more on my level, and I am.” His eyes were still laden with apprehension. “I thought that maybe you liked me, too, but then Avery went off to college and you didn’t say anything so…” She sighed. “This is just me, being completely open and honest with you about the fact that I might’ve been expecting too much from you without even letting you know about it. When you reacted badly to Logan and I dating, I thought that _maybe_ I wasn’t crazy and you _do_ have feelings for me, but then you only really got mad at the Avery thing so…”

She shook her head, taking another deep breath to carry on. “I just wanted you to know that I’ve let all of that go. I must sound absolutely ridiculous talking to you about this and you probably think I’m speaking nonsense because I know you don’t feel that way about me.”

“I didn’t say anything, Rory,” Jess said, voice tight and quiet almost as if he were trying to keep himself calm.

“It doesn’t matter, anyway. I’m with Logan now, and I _like_ Logan—a lot. I know that you think he’s a bad choice for me, but he’s really been so good to me these past few weeks and I’m just… I’m really happy, Jess.”

Jess rubbed a hand up and down half his face. “That’s great, Rory, really.”

“Sorry for unloading all of that on you.”

“Not a problem.”

“Are we… okay now?”

Jess shrugged. “Sure.”

“I’m sorry for what I said about Avery. I know she wasn’t just some girl to you. You really loved her.”

“Yea, I still do.”

“Right. Of course. You guys weren’t like Dean and I where you had one foot out the door. You were happy and in love the way couples _should_ be, it’d make sense that you still love her.” His words shouldn’t have hurt, but they did. She couldn’t help looking at the book of Neruda poems on the table and feeling a little constricted. Rory licked her lips and nodded, more to herself than to him, getting up to her feet with a fake smile. “Well, I’m going to go get a cup of coffee. You know us Gilmores.”

“I do.”

“I’ll be right back,” she said with fake pep, reminding herself that she was happy with her new relationship as she read the menu board.

 

**AGE TWENTY-THREE. JUNE. PHILADELPHIA**

The third round was the most conventional. They’d wound up on the bed kissing, though not as heatedly as before. Rory nipped at Jess’ lips with her teeth, not hard enough to draw blood, but enough to leave bruises. She explored his mouth a little slower now, and let him take over when he wanted to. She was laying on her side and he was caressing her hip with his thumb as she stroked him nice and slow. He wasn’t quite hard yet, but he was definitely getting there.

Jess broke their kiss to bite and lick at her neck, definitely intent on leaving marks, but she didn’t mind. She draped a leg across his and ground into him the way she had long before they’d decided to make things official. Rory whimpered at the contact and undulated her hips in a circular motion against his hip.

“God, you are so wet,” Jess said against her neck. “I feel it against my thigh.”

She moaned in agreement, grinding down a little harder and the sound of her skin against his made a squelching noise that’d probably embarrass her when she wasn’t so turned on.

Jess pressed her into the mattress on her back and slipped two fingers into her with ease, pumping in and out with the tips curled to hit her g-spot and she grabbed him by the back of the neck and brought him down to kiss him. Rory spread her legs a little further apart, almost on the brink of tears when her orgasm approached and Jess moved his fingers a little faster, not so much pumping as he was just rocking back and forth until stars burst behind her eyes and her back arched, toes curling as she screamed up to the ceiling.

He removed his fingers from her slowly and licked her juices off his fingers before she grabbed his hand and took them into her mouth instead, making a show of sucking them off and applying the same pressure she’d used on his cock earlier. Jess leaned down press himself against her, now fully hard again.

“I want you so fucking bad.”

“I’m right here,” she teased, pulling him in until their cores met. “So, fuck me.”

He stared at her for a moment, almost as if he weren’t sure that she’d really said those words, but she just stared back, daring him to do something. “Say that again,” he demanded.

That wasn’t what she was expecting and she flushed, but she refused to lose her nerve. “I said, _fuck me._ ” She wasn’t particularly used to dirty talking but it seemed like Jess really liked it, and for the first time ever it really seemed to be working for her, too. “I need to feel you inside of me… I don’t even want to be able to walk tomorrow.”

“Fuck, Rory.” Jess groaned at her wordsand reached over into his dresser to grab a condom. Rory took it from him and rolled it on, keeping her hold on him as she circled her wet entrance with his cock and moaned as she rubbed the tip up and down her clit. He watched her, unmoving until he took her breasts into his hands again and started to knead them as she teased the both of them where they needed relief the most.

Finally, he pulled back from her and took himself into his own hand. Rory stared up at him curiously but closed her eyes as he finally pushed into her. When he was all the way in she squeezed him and he groaned above her, pulling out against her vice grip and pushing back in. It felt so good that they were both moaning together at once, and then Jess kissed her, soft and sweet and Rory felt herself melt into their mattress. He grabbed her right leg and lifted it up to rest on his shoulder and then he pushed in deeper, and Rory snapped her hips forward unable to take it anymore. Jess read her cue and started to move, nice and slow at first until he worked his way up to a moderate pace that had them both panting and moaning nonsensical words.

“Don’t stop,” Rory chanted, moving her hand down to touch herself in tandem with his movements.

He grunted, throwing her leg off his shoulder and spreading her legs far apart so he could fit between them, but his thrusts were angled a little higher and they hit Rory perfectly.

“Yes, yes, yes,” she panted, bringing him down to kiss her. She bit his tongue in her passion but she couldn’t help it. Her hips started to raise off the bed in her fourth oncoming orgasm of the night. “Right there, right there, right there!”

“You’re so tight, babe,” he whispered into her ear. “You feel so fucking good. I’ve wanted this for so long, I’ve fantasized about it, wondered how you tasted, the way you moan,” he kept his original thrusting pace and it kept Rory on a high she didn’t think was possible, “I’ve thought of every little fucking detail.” He flicked her clit repeatedly until her oxygen ran out and she could no longer speak and her eyes were squeezed so tight she wasn’t sure if she’d ever be able to open them again. She came with a silent cry at his words and ministrations, her body convulsing and her walls tightening around him so hard that he almost collapsed on top of her.

Jess thrust a few more times until she felt his signature twitch and he came with a long winded, broken moan against her ear and Rory locked her legs around his back to keep him with her for a moment, and he twisted so he could lay on his side without crushing her.

When she felt a bit calmer, she looked into his face and smiled a little shyly when he wrapped an arm around her waist and brought her in close to his chest. “I’ve never dirty talked like that before…”

“No?” He asked, wiping away some of the sweat on her forehead. “You’re a natural.”

“I liked it,” she squeezed her walls around him again, still enjoying the feeling of him inside of her.

He licked her earlobe in appreciation for her action. “I’m glad.”

“I also liked when you told me that you used to fantasize about me… That was really hot.”

He shrugged, placing a loving kiss on her nose. “Well, I did.”

“How often?”

“An embarrassing amount.”

Rory smiled. “I fantasized about you, too. I felt guilty because I was in relationships but,” she shrugged. “You were always a sexual fantasy for me.”

“Do I live up to the hype?”

She laughed. “I think you surpassed it.”

Jess hummed in appreciation.

“And what about me?” She asked, poking him in the arm.

“Oh, you _definitely_ surpass the hype. You let me fuck your mouth, that is… insane.”

Rory grinned, feeling a little embarrassed but proud of herself all at once. “And…” she started, but instantly regretted her thought process, but this was something she had to know. “This isn’t _just_ sex, right?”

Jess grabbed her hand and peppered little soft kisses along her knuckles and then turned it over to do the same thing to her palm. “This is more than just sex to me, Rory, I promise.”

“And you enjoyed the date? The Magic Garden and the bar? I already know you enjoyed this part, so…”

“I enjoyed every minute of our date,” he promised, and his voice was so uncharacteristically soft that Rory felt herself turning into goo.

“Okay, good… One day you’ll have to tell me what you fantasized about so I can do it for you,” she said, feeling emboldened.

Jess smirked against her brow and placed a soft kiss there. “Only if I get to do the same for you.”

“Oh, absolutely. I’m a very selfish lover, couldn’t you tell?”

Jess chuckled, but he didn’t banter back. She leaned back in his arms to look up at him only to see his eyes were closed, so she cuddled a little closer and closed her eyes for a moment as well, running her fingers up and down his back. She was really enjoying this new level of intimacy between them. They’d obviously always been close, but she’d never stroked the back skin of his back, and he’d never held her so tightly around the waist while her naked body pressed into his. She was so comfortable in the circle of his arms that she was tempted to fall asleep right then and there, but she knew needed to at least get up and brush her teeth and Jess needed to dispose of the condom.

As if reading her mind, Jess pushed himself off of her with a groan and slipped out. She felt oddly empty without him now. He leaned back down to kiss her nice and slow, sipping at her lips as he ran his tongue along her teeth. She shivered when his tongue caressed hers, but it was gone too soon. Jess ended the kiss with the capture of her upper lip and then he kissed again, this one more chaste before he left for the bathroom.

She got up and viewed the aftermath of their night, feeling embarrassed at seeing their clothing items all scattered around the apartment. Rory quickly grabbed Jess’ boxers from the hallway and started to pick up the other items as she went along. She carried it all back into the bedroom and threw it into their hamper and then made her way back out to heat up their left overs. Jess was out of the washroom while the food was in the microwave so she’d slipped in there quickly and got out just as the device beeped. She grabbed their food and came back to bed to find Jess up and waiting for her.

“Well, well,” he teased, his eyes raking over her naked body, and despite what they’d just been doing, Rory blushed. “Someone brought sustenance. Hoping to get lucky again, Gilmore?”

“We burned a lot of calories just now,” Rory defended, suddenly feeling a little shy as she sat next to him.

Jess laughed. “We definitely did.” Rory watched him as he grabbed a chicken wing and bit into it, licking the sauce off of his lips. “Like what you see?” He said, after swallowing and Rory found herself nodding.

She wasn’t the only one who’d been too lazy to cover up after. He chuckled though it quickly turned into a hiss once he dropped some hot chicken onto his chest. Rory crawled toward him and licked the remaining sauce off, dragging her tongue toward his nipple and circling it the way he’d done with hers.

“Your libido is out of this world,” he teased.

Rory looked up at him. “Are you complaining?”

“Not in the slightest.”


	8. Chapter 8

**Notes for the Chapter:**

> Sorry for the lack of updates, I've been sick like a dog, but I'm good now and here's the next chapter.  
> It hurt me to write, but I hope all of you like it! Don't worry, Lit remains happy in 2008 but we've got some major Logan drama going on right now. I won't blame any of you if you cry at Jess' monologue to Lane at the end of this chapter.
> 
> As always, please leave me a comment bc I love to know your thoughts and talk to you guys!

**AGE TWENTY. JUNE. HARTFORD**

Jess really didn’t like being at the Gilmore mansion.

For all intents and purposes the house made him feel uncomfortable. He was not, by any means, cut out for this high society lifestyle, and everyone in the community knew he didn’t belong here. Emily accepted his presence on behalf of her granddaughter, but Jess knew her well enough to know that she didn’t actually approve of him at all—add that to the already incredibly long list titled _Reasons Why Jess Mariano Could Never Be With Rory Gilmore._ The elder Gilmore always smiled at him placidly, opened the door to her home, and then called Lorelai up to complain before he was even out of ear shot. Luckily, he was used to it by now.

He’d been to the mansion at least fifteen times since Rory had moved in here after the big fight with Lorelai in May. Had he been a more self-preserving person, he would’ve avoided coming here, but there were plenty of things he’d do for Rory Gilmore, and withstanding discomfort and the abuse of her grandmother just so happened to be on the list. He was just grateful she was living out in the pool house, so he didn’t have to be in Emily’s presence for too long.

The pool house was nice. He’d always thought so, really, and he enjoyed the time he spent in it. It almost felt like it didn’t belong to the Gilmore’s with the way he and Rory had a tendency to make it their own. He’d lounge on the couch, on the rug, or sometimes on her bed with a book. They’d watch TV and have a small cocktail together, careful not to use up too much of the alcohol lest they wanted Emily to have a fit. It was cozy, but more than anything it was just nice to be the two of them in such a beautiful setting. It felt oddly domestic, and Jess enjoyed it a little too much.

Currently, Rory’s head was resting in his lap and he idly stroked her hair as he read. She had a boyfriend, but that’d never really stopped her from getting comfortable on his lap before. It got awkward sometimes, his mind would wander to inappropriate thoughts, and it’d take his mind off of his book and make his jeans a little tighter. He could never be certain if Rory noticed, but sometimes he thought she twisted her head toward his erection with curious eyes just to torture him. Thankfully, they seemed fine right now. Rory had her laptop propped on her thighs and hip, her fingers scrolled through views of apartments and she _hmm_ ’d her satisfaction or disapproval, and Jess kept his attention primarily on the words in front of his face.

“Hey, what about this one?” She wiggled her head closer to his stomach to get his attention.

Jess put his book down for a moment, keeping the page with his thumb as he turned his head to look at the screen. She was showing him a nice, airy looking apartment with dark floors but lots of windows and white cabinets. “It’s nice,” he said easily.

“We could rent it! You have two jobs, I’ll get one and we’ll split the rent,” Rory said, sounding very excited.

“Rory, we’ve talked about this. You and I can’t move in together.“

“Why not?” Rory pouted up at him. “I’m not going back to my mom’s and I dropped out of Yale, I can’t live with my grandparents forever.”

“You’re going to go back to Yale,” he said firmly. “You _love_ Yale.”

Rory crossed her arms over her chest, scowling. “Not anymore.”

“You can’t let one guy ruin your whole experience.”

“He told me I’ll never be a journalist. He said I don’t have it!”

Jess groaned. “Rory, _come on_. You can’t take that guy seriously!”

“He’s been in the industry longer than you and I have been _alive,_ Jess _._ I think he’d know if I’m good enough or not! Plus, I’m a criminal now. I’ve defiled myself completely. No one will ever take me on as a serious journalist. ‘ _Oh, look at that girl with the criminal record. She has little to no impulse control, a total flight risk’_ is what they’ll say about me!”

“Rory,” Jess said, nudging her to get up so he could get a better look at her, but she didn’t move. He sighed, and looked down at her. “I know you think Mitchum Huntzberger is the be all-end all, but he’s _not_ , okay? He’s not. You weren’t even a journalism-based intern, he literally just had you shadow him, so how would he even _know_ if you’re a good journalist or not, huh? It not like you were writing stories for him. Look, if _you_ decide that you don’t want to be a journalist anymore then okay. You know I’ll support you, and Lorelai will, too, but don’t just let this one negative comment kill your dreams _._ ”

“You don’t get it, Jess!” Rory said, finally sitting up to look at him. “I had this one dream my _whole life_ and I was told that I was born for it, and then I get into the actual industry only to be told the exact opposite. What have I been doing with my life then?!”

“You’ve been reaching for the stars! Studying hard, _fighting for your dream._ Rory, this journalism thing isn’t just going to fall into your lap, you have to work for it.”

She paused at that, studying him with a look he quickly decided he didn’t like; it reminded him of her grandmother, cold, calculating and most definitely wicked in nature. “What would you know about working for anything? You don’t even go to college!”

Rory had been saying stuff like this often since quitting Yale. Her frustration with herself was mounting in ways that was starting to unleash on other people, and Jess always happened to be her main target. He’d learned after the first time that it was just better to take it. If he fought back they’d both blow up and go without talking for days.

Jess took in a deep breath, held it for five seconds and let it go. “I’m not fighting with you about this again.”

She stared at at him for a moment and suddenly Emily Gilmore was gone and Rory, in all her soft-edged glory was back. Her face crumpled and her bottom lip wavered as she stared up at him with big Bambi eyes. “Oh my god,” she said thickly. “I can’t believe I did that again! God! Jess, I am _so sorry._ I didn’t mean it! You know I didn’t mean it, right?”

He nodded. “Mhm. I know.”

“I’m just so frustrated with everything! I don’t mean to take it out on you,” she got up to pace then, laptop forgotten on the couch, “you don’t deserve that and I’ve been doing it so often! You work _so_ hard, Jess. You graduated when no one thought you would, and you’ve stayed in Stars Hollow for a lot longer than anyone thought, too.” Her hands were flailing wildly as she rambled, and Jess had to keep himself from smiling at her. “Plus, you work _two_ jobs—the diner _and_ the book store. You bought your own car, you’re saving up for your own place. How could I say you’ve never worked for anything? God! What is wrong with me?!”

“You’re just stressed.” He stood up, forgetting all about his book, and grabbed her by the shoulders to keep her still. “It’s going to be fine, Rory. Breathe.” She closed her eyes and took in a deep breath and he smiled. “That’s it,” he encouraged, “a few more.” When she was done, she opened her eyes and thankfully seemed a lot calmer. “You good?”

Rory nodded. “Yeah.”

He slipped his hands down her arms and to her wrists, which he gave a gentle squeeze. “Good.”

“I’m sorry, Jess.”

“I forgive you.”

“You do?” She looked as unsure as she did every time this happened.

Jess squeezed her wrist again, fighting against the urge to take her hand and kiss her her knuckles. They may have been affectionate, but there were boundaries they still shouldn’t cross. “I do.”

She tugged her wrists free of his hold to hug him and he wrapped his arms around her back, enjoying their close proximity a little more than he should have.

 

**AGE TWENTY-THREE. AUGUST — ART GALA. NEW YORK**

Rory hadn’t realized how much she’d missed New York until she stepped back into it, and she knew that Jess felt the same way.

She loved the way his eyes lit up at the tall buildings, the old street signs, and some of his favourite landmarks. Matt and Lane hooted and hollered excitedly behind them in the taxi van, pointing out some of the more touristy things that Jess and Chris hated. There was a sheer irony in the both Chris and Jess being from New York and growing up in the neighbourhood but never having met until their adult life. Rory was certain that just meant that they were destined to meet.

“Don’t say that,” Jess had said, shivering in disgust, “you sound like my mother.”

And, so, Rory had never repeated it again, but she still believed that fate had most certainly played a role.

When they arrived at the hotel, Rory was taken aback by the monumental size of it. It was a beautiful glass building with gold ornament decorations on the outside, and it seemed _really_ fancy. When she took in what street they were on, she quickly realized that this was the address of the Gala _in general_.

“You didn’t tell me we were staying at _this_ hotel! Can we even afford this?” She looked up at the building and took it all in again. “It’s very… _Gilmore._ ”

Lane nudged her in the side. “Well, it’s a good thing you’re a Gilmore then. You should be used to this.”

Rory shook her head. “Not really, Mom never let me bask in any of this growing up. It’s still a little weird to me, even after dating a Huntzberger.”

Jess wrapped an arm around her waist and placed a sweet kiss to her temple. “Our rooms are paid for by the Ramesh’s.”

“What?” Rory asked, wiggling out of his arms. “Jess, that’s _a lot_ to accept.”

“I, for one, am very happy to accept it,” Matt said easily, bounding past them with his suitcase. “You think they’ll be any hot, single chicks here?”

Rory groaned, hand to her face as Jess led her inside to check-in. “You can’t bring Matt anywhere.”

Chris laughed. “She’s not wrong. That boy is not made for the lavish.”

By the time they got into their room, Rory was exhausted and a little happy that it was just her and Jess for now. The Gala wasn’t until the evening, and they’d reached the hotel by mid-afternoon, which gave her the perfect time to take a nap. Jess seemed to have the same idea as he stripped down to practically nothing and gathered her up in his arms when he made it into the bed.

“This mattress is amazing,” he mumbled into her shoulder and she smiled, stroking the hair on his arms. “We should get one like it for the loft.”

“I definitely wouldn’t complain.”

He kissed her neck and the spot behind her ear before sinking back down into her and falling asleep. His chest rumbled with his snores and Rory leaned back against him and closed her eyes for a wink of sleep.

It was a series of knocking and Avery’s voice calling to them that woke them both up at least an hour later.

Jess mumbled incoherently but he told Rory to stay put as he went to answer the door in nothing but his boxers. When Rory pushed herself up to see what was going on, Avery was in their room looking glam in a long, strapless dusty rose pink gown, though her eyes were too bleary from sleep to take in all the details. Still, she was sure Avery looked gorgeous. She always did. Rory pulled the covers up around herself a little firmer, knowing she was fully dressed but she still felt a little embarrassed at her current state.

“I just came to bring you guys complimentary champagne,” Avery said, holding up a big, dark green bottle. “It’s a _thank you for coming_ gift.”

Jess took it from her, studying it for a moment before he put it down on their dresser. “Wow. Thanks.”

“Yeah,” Rory said awkwardly. “Thank you.”

Avery smiled at the both of them, patted Jess’ shoulder and made her way back to the door. “I’d start getting ready soon. Gala starts at six. It’s almost five now.”

When she was gone, Rory laughed to herself and flopped back down onto the pillows. “That was embarrassing.”

“It wasn’t that bad,” Jess said, wandering into the bathroom without closing the door. She heard him put the toilet seat up and the sound of him urinating came soon after. It felt really natural, all things considered. They didn’t have their own private bathroom back at the loft, but she figured if they did then this is what it would be like. Domestic and sweet.

She got up from the bed to sort through her suitcase for her dress and makeup as Jess washed his hands. They met in the doorway of the bathroom and Rory playfully scowled as he blocked her way, his hands on her hips. “I need to do my makeup,” she said, giggling through her fake seriousness. Jess leaned down to nuzzle her neck and kissed along her jaw before his mouth found hers and she almost dropped her makeup case.

Rory broke the kiss with a pout. “Jess, we have to get ready. I can’t have your wandering hands distracting me.”

“Okay, okay… But you know what could be fun?”

She eyed him warily. “What?”

“You, at the counter doing your make up totally naked—“

“ _Jess_ ,” she scolded.

He shook his head, smirking. “Hey, let me finish. You, at the counter doing your makeup totally naked, and _me_ , on my knees going down on you while you do it.”

Rory shook her head, though her body reacted involuntarily to how good it sounded. “Nope, can’t happen. Lane and I have to do our hair and makeup together. It’s girl code.”

“Why do you always ruin my fun?” He pouted and she kissed him.

“Sorry.”

He grunted at her just as Lane came knocking at the door. Jess moved to open it and Chris, Matt, and Lane all filtered in.

“Whoa, what were _you two_ _doing?_ ” Matt teased, eyebrows wiggling.

Jess rolled his eyes. “Sleeping.”

“Uh huh,” Matt hummed, leaning into Chris to stage whisper, “ _Sleeping_ is code for _seeeeeex_.”

Chris shoved him a bit. “If they were having sex they’d just say so. Not like they ever hide it when at home, why hide it on vacation?”

Rory blushed. “Hey! We try to be respectful…”

“Oh yeah,” Chris said, rolling his eyes, “totally respectful with all that moaning and screaming. I think you guys think you’re being quiet, but you’re really not.”

Rory fanned her face, grabbing Lane by the wrist to tug her into the bathroom. “We’re getting ready now. This is girl’s only zone, so stay out!” When she shut the door, she found Lane giggling behind her hand. “Not you, too! Please, Lane.”

“Oh, Rory, come on!” Lane said, still laughing a bit. “This is _me_ we’re talking about. If anyone knows how badly you’ve wanted to be with Jess it’s me. You had a Jess vibrator.”

“I did not!” Rory denied, her face so hot she thought it was going to melt off her skull. “Paris got me a vibrator and said to use it when thinking of Jess, but I never used it!”

Lane threw her a look. “Really? Not even once?”

Rory looked down at her feet, wiggling her freshly painted toes. “Well, okay, _maybe once_.”

“Mmmhm,” Lane said, placing her makeup bag down on the counter. “That’s what I thought.”

“Oh, shut up,” Rory said, unzipping her makeup bag to look for her foundation primer.

 

**AGE TWENTY. AUGUST. HARTFORD**

With every passing day, Jess was getting a little more fed up with Stars Hollow.

Taylor was insufferable, Dean had gotten _married_ (the fool), and Kirk was even more annoying that usual. Miss Patty and Babette were constantly asking him questions about Rory and he could see Lorelai skulking around hoping to overhear his answer. Jess felt stifled, and he couldn’t believe he was still stuck here at age twenty. He yearned for freedom, but he didn’t quite have the ability to break his chains just yet. The worst part of all, was that Liz had found her way back into town permanently.

His mother waltzed into the diner looking peppy, sat on a stool and announced to him and the whole diner that she and TJ had officially bought a house. He hadn’t reacted, did his best to keep his face impassive, but his tendons were stressed from holding the coffee pot a little too tight. When she hadn’t got the reaction she’d wanted, Liz followed him around the diner, talking at him until he said something. Jess managed to hold it together until he told Luke he was heading out for his break, but Liz had followed him to the town square.

“I don’t understand why you just won’t talk to me?” Liz said, close on his heels. “I’m your _mother_ and I just shared some really good news with you! You think you’d be happy. We can finally be a family again! Isn’t that exciting?!”

Jess spun to face her, eyes darting around to scan their surroundings before he ripped into her. There were a few people within earshot so he kept his voice low. “I don’t want to be a family with you, Liz. If it were up to me, I’d never see or talk to you again, but Luke seems to like you, guess whose forced into being polite? That’s right, me.”

“Jess, I’m your _mother_ ,” Liz said again.

“You keep saying that word as if it means something.”

“It does!” She said, glaring at him. “I gave _birth_ to you! I took care of you!”

Jess laughed. “Good one on the take care part.”

“I did my best! And I’m better now, just give me a chance.”

“No.”

“Jess—”

“I said _no!_ I’m not giving you a chance to make it up to me. There’s nothing you could ever do to make it up to me, so just stop trying,” Jess begged of her; he really didn’t know how much more of this he could take.

Liz Danes exhausted him, and he’d never been any good at dealing with her. She made him feel scared of the world. The things that she’d shown him and forced him to experience at a young age hadn’t hardened him as it’d had ruined him. In a way he felt like a caged bird.

“I get that you’re mad at me,” Liz said, putting on her best self-pitying voice. “But I just think we could really be happy—you, me and TJ—under one roof. It’d be like old times, but better! Besides,” she said leaning a little closer, condescension filling her eyes, “don’t you think it’s time you stopped mooching off your uncle?”

Jess scoffed and stuffed his hands in his pocket. “Is that what you think I’m doing? Mooching off of him?”

Liz shrugged a bit. “My brother is a very nice man. He’d do anything for family, include take care of his bum nephew. Come home, baby… You know that I’m the best person to take care of you. Your uncle is _good_ and he deserves to be happy, he shouldn’t be worrying about his washed-up, never going to college nephew. But you and me? We’re like peas in a pod! Don’t you think you’ve thrown more than enough wrenches into Luke’s life, honey?”

He took a step back from her, regarding her with the utmost disgust. In the years he’d been away from her, he’d forgotten how cruel she could be with her words. The way she told him about her expectations of him with a casual flair. She didn’t care that it hurt him, didn’t care that he was trying so hard not to be _anything_ like her. “I don’t want anything to do with you,” he spat, “so just stay the hell away from me if you know what’s good for you. _”_

Jess turned back on his heel and stalked off, heading toward the old bridge.

Liz yelled after him, _“You’ll always be my son! Nothing will ever change that!”_ but it just made him walk faster.

_—_

_“_ Ah, Jess!” Mr. Ramesh called out to him. “Just the man I wanted to see.”

Jess looked up from staring at his reflection in the water, he hadn’t brought a book with him when he’d taken his break to get away from Liz, so he was passing the time by getting lost in his own head. “Ajmal,” he said simply, nodding. His old teacher’s first name still felt foreign on his tongue, but he was getting more accustomed to using it now.

Ajmal took a seat beside him on the bridge, but he didn’t look at him. “You seem blue.”

“You said you wanted to see me?” Jess tried to evade, but Ajmal saw right through him.

“I did, but your mood takes precedence. What happened?”

“Just some stupid shit with my mom.”

Ajmal hummed. “Ah, yes. Your mother. A tumultuous relationship, no?”

“Yeah.”

“Would you like to discuss it?”

Jess laughed, so thin and wane it barely seemed to last a second. “No. Can you just… tell me what you need? Not to be rude, I just… _can’t_ , right now.”

“Understandable,” Ajmal said, swinging his legs back and forth over the bridge. “I was talking to a few of my contacts out in Philadelphia, and one of them is looking for his next book to publish, asked me if I had any students who liked to write. You came to mind immediately.”

Jess’ mouth ran dry and he turned to look at Ajmal. “I… I appreciate that, but…”

“You’re not ready, I know,” Ajmal said, nodding along in agreement. “Unfortunately, I don’t disagree… but I’d still like you meet him. It doesn’t hurt to network, Jess.”

It seemed like a once in a life time opportunity, and he _was_ itching to get out of Stars Hollow, but there were other things he had to think about, too. Like, Luke, Lane and Rory. The diner. His job at the book store. Rory. Everything kept circling back around to Rory in his mind and the more he thought about it, the worse he felt. She’d been so angry at him the last time he’d left, but that was because he didn’t have the guts to talk to her about it first.

Luke was his secondary concern. He didn’t believe a word his mother had said, or, at least he tried not to, but there was a small part of himself that agreed with her. It was high time to leave Luke’s nest. He’d been with his uncle long enough, and though he knew Luke would never complain, Jess couldn’t work and live above the diner forever.

He bit his lip. “I’ll think about it.”

“Time is of the essence, my boy,” Ajmal pat his back firmly. “Don’t wait too long. He says he’ll keep his window open for you until December at the latest.”

 

**AGE TWENTY-THREE. AUGUST — ART GALA. NEW YORK**

“Hey, so you said Avery’s mom is Black, right?” Chris asked just as they loaded onto the elevator, but Jess barely took the question in, too distracted by Rory to pay attention to anything else.

She and Lane had went out shopping for a dress sometime in July, and she’d refused to show him what she’d bought. In a way he was grateful because he got to take her in with fresh eyes. She was wearing a really beautiful royal blue number that trailed after her a little when she walked. It was modest in the front, but form-fitting with a low back to show off some skin. She’d even bought him a matching tie. He definitely felt a little prom-y, but he knew that’s what Rory wanted, so he didn’t complain.

“Jess, stop drooling over your woman and answer me,” Chris said, elbowing him hard.

“Ow, what the fuck.” Jess glared at him. “What do you want?”

“He asked if Avery’s mom was _a sista_ ,” Matt said, earning him a glare from practically the whole group.

“Don’t say _sista,”_ Chris demanded. “It’s racist when you say it.”

Matt pouted. “Fine. Sorry.”

Jess rolled his eyes. “Yes, Chris, Avery’s mom is Black.”

Chris nodded. “Cool. It feels nice to support my people. Feels even _nicer_ to know Black people can host fancy ass Gala’s for rich people. We’ve made it! Or, well, some of us have.”

The elevator doors opened up to the ground level, and they were met by two men in tuxedos. Rory mumbled something about Gilmores and Huntzbergers that Jess couldn’t quite catch. He held his hand out to her and smiled when she took it, following the men through the lobby and into a grand party room decorated in with some of Mrs. Ramesh’s artwork, fancy looking hors d’oeuvres, and little crystal animal trinkets every where.

“Wow,” Rory breathed out beside him, taking it all in. “This is fantastic! I want to look at the artwork!” She dragged him off easily to one of the paintings of a tiger set up.“This is so beautiful! You never told me she was so amazing!”

Someone laughed behind them and they both turned to see Terra Ramesh in the flesh. “Well, I’m glad someone likes it.”

She looked the same as he remembered; tall and regal looking, her natural curly hair always worn straight but curling at the ends. Mrs. Ramesh was a lighter brown than her husband and Avery, and she had a rectangular face with large, almond shaped eyes. She kept her body in tip top shape and always dressed like a business woman ready to go in for the kill.

Jess smiled a real smile at her. “Mrs. Ramesh,” he greeted.

“Jess,” she was almost grinning, “may I get a hug?”

He let go of Rory’s hand and made a show of putting on a sigh. “If you must,” he said playfully, but he leaned into her hug all the same. Liz Danes had been the worst mother he could’ve asked for, but Terra Ramesh had taken her place in the best possible way.

“You look good,” she said before her eyes moved onto Rory. Jess grabbed her hand again and tugged her forward a little, knowing she was nervous. “Wow, if it isn’t Rory Gilmore. Avery did tell me you were coming, but I feel like I haven’t seen you since you went to Stars Hollow High.”

Rory laughed a little nervously and Jess gave her hand a firm squeeze which seemed to ground her. “It has been a while,” Rory said, tucking a strand of hair behind her ear. “It’s very nice to see you again. This Gala is absolutely phenomenal, and your artwork? It’s even _more_ than phenomenal! I was just about to tell Jess that your use of colour and contrast could be compared to Henri Matisse! It might even surpass him, honestly.”

Jess’ smile grew as Rory rambled on, and Mrs. Ramesh’s eyes lit up at her use of technical terminology and reference to famous artists. His heart was just about ready to burst with pride when he recognized that spark of approval in Mrs. Ramesh. She glanced at him, smirking.

Finally, Rory finished, her face red and her free hand back at her side. “Sorry, I never talk this much,” she said and Jess snorted.

“Trust me, she does,” he countered and Mrs. Ramesh laughed.

“I’m honoured that you think so highly of my work, Rory.”

Rory nodded vigorously. “Oh, I do! I’d love to commission you someday, if you do commissions that is. It would be so fantastic to have a Ramesh original in my home.”

“You flatter me too much,” Mrs. Ramesh said.

“Mom!” Avery called out from behind her, and Jess watched as she came over, hand in hand with another woman, her heels clicking hard against the floor. “There you are! I’ve been looking for you. Oh! Rory, Jess. Hi.”

Jess raised his chin in acknowledgment.

“Hi again,” Rory said.

“This is Kimberly Díaz,” Avery said, gesturing toward the girl beside her. She was beautiful in Jess’ opinion; a little taller than Avery with long, perfectly curled dark hair, deep olive skin, and dark brown eyes. Her dress was a cream colour with a high, sleeveless neckline that showed off her thin arms and dainty shoulders. “Kimberly this is Jess Mariano and Rory Gilmore. You’ve already met my mom, obviously.”

“Nice to meet you,” Kimberly said, holding out her hand to Jess.

“Likewise.”He shook it lightly before she moved on to Rory.

“Come on,” Avery said to her mother. “I want to show Kim the showroom.”

Mrs. Ramesh looked at Rory and Jess with an apologetic smile before bidding them a short goodbye with a promise to hopefully catch up with them later.

Jess turned back to Rory to find her looking bewildered. “What’s wrong?” He asked, tugging her a little closer to him and placing his free hand on her waist.

“Was that… Avery’s date?”

“Oh.” He laughed. “Yeah, probably.”

“So, Avery likes girls?”

“From what I know? Yeah.” He brushed some of her curled hair back from her face.

Rory blinked at him. “I didn’t know that.”

“I wouldn’t have expected you to.”

“You never said.”

“Is it important?”

She hesitated, mouth open as if she wanted to say something, but brow creased as if she didn’t know what to say. “No, I guess not… She looks pretty tonight, though.”

Jess raised an eyebrow at that. “Rory,” he said, treading lightly. “Are you attracted to Avery?”

The way her face turned red gave away the answer, but Rory shook her head vehemently and avoided his gaze. “No! Girls are allowed to find other girls, pretty.”

“I know, but you literally said it right after finding out she’s into girls.”

“I,” Rory faltered. “That doesn’t mean anything!”

Jess ran his finger along her chin, rubbing her subtle cleft softly. “It doesn’t have to, but it _might_. It’s okay if you have a little crush.”

“Are you just saying that because you’re hoping for a threesome or something?”

He rolled his eyes at the accusation. “I’m not that selfish, Rory. Chris says sexuality is fluid and I am inclined to agree with him. We’re twenty-three years old, it’s okay if you’re just now realizing you might have an attraction to women. Or, at the very least, just an attraction to Avery.”

“Okay, but…” Rory looked up at him, her eyes swimming with this new information. “I… ”

Jess shook his head. “We’re not going to go through this right now. We’re going to enjoy this Gala, stuff our faces with some weird, fancy food, and avoid any existential crisis’ in regards to sexuality. We can talk about it later if you want, okay?”

He watched as Rory took a deep breath, let it go and then nodded firmly. “Okay.”

 

**AGE TWENTY. OCTOBER — RORY’S BIRTHDAY. STARS HOLLOW**

Rory was amazed that Jess was here.

She knew her best friend well enough to know that he didn’t really like hanging out in groups, specifically in groups that included her Yale friends. She’d begged him to come tonight for her post-birthday celebration, switching on the water works and tugging on his hands—it worked every time. The tears hadn’t all been fake, anyway.

Her birthday party had been awful despite the effort put in by her grandparents. She and her mom were still on the outs and it didn’t look like they’d be mending fences anytime soon, so Logan had suggested going out to drown her sorrows a little more. And now, she had Jess sitting across from her, looking tired and bored as Colin and Finn heckled a jazz singer on stage.

Rory smiled at him, hoping he could make it through the night. Jess had a lot more beers than usual, and this was really only her second time seeing him drunk, he seemed grumpier than the other time as he stewed in his anger and general annoyance at everyone and everything.

She reached across the table to grab his hand. “You okay?” She asked.

His dark eyes took her in for a moment, lingering with something she couldn’t identify before he pulled his hand away. “I’m fine,” he said, taking a big sip of his beer just as the singer finished up a song and people clapped.

Rory had hardly being paying attention to the performances all night. Jess was here for once and his presence was commanding all her attention. She liked the way his gaze stayed on her, as if he were watching her to make sure she was okay. Juliet and Rosemary had been watching him, too, they’d cornered her in the bathroom and asked for all the details on him in a very Madeline and Louise situation, but Jess hadn’t noticed them and Rory liked that, too.

“Everything okay over here?” Logan asked them, leaning in close on his elbow. His eyes were narrowed in suspicion and Rory knew what he thought, it was _exactly_ what Dean had thought about them, too; that they were too close, too affectionate; that they were more than just friends.

“Everything’s fine,” Rory said coolly, and his look remained for quite some time before he backed off with a shrug and returned to whatever foolishness he was doing with his friends.

“I need some air,” Jess said to no one else but her, and it sounded like an invitation.

“I’ll go with you,” Rory said, reaching for her jacket. Logan didn’t argue.

The night air was cool and crisp on her skin, it smelt clean, too. Rory took a deep breath of it, trying to enjoy as much of it as possible before she had to go back into the stuffy pub. Jess didn’t say anything as he leaned against the pub gate, his head tipped back as he looked up at the black sky. Rory studied him silently, admiring the hollow of his throat but she didn’t let herself get caught up in it.

“It’s pretty tonight,” she said, hoping to strike up conversation.

“Yeah,” Jess said, slowly letting his head come down to look at her. “I’m thinking I might move to Philly.”

Her brow creased. “Wait, what?” She asked, hardly able to grasp what he’d just said. It just seemed so random. “Why?”

Jess shrugged. “Ajmal has some publishing contacts out there, he wants me to network with them. I haven’t decided yet, it’s just an idea.”

“Publishing?” Rory wrinkled up her nose in confusion. “I didn’t know you were interested in publishing.”

“I think I could do it, and they’re willing to talk to me without any real experience. Show me the ropes, possibly give me a job if I’m a good fit. I don’t know, it’s better than what I’m doing right now. It seems cool.”

Rory stuck in her hands into the pockets of her coat so she didn’t fiddle. “Are you excited for it?”

“Kind of.”

She forced herself to smile, desperately wanting to be happy for him. This was good news, she told herself. Jess was finding his passion and he was going to do great things, just like she knew he would.

“A little scared too, maybe?” She offered, and he shrugged again. Rory smiled for real this time. “It’s okay to be scared of change,” she reassured him, taking a hand out of her pocket to reach for his. She intertwined their fingers and gave him a little squeeze, squeaking when he pulled her close, hip to hip and wrapped an arm around her waist.

“You’re not mad?” He asked her and she could smell the craft beer on his breath.

“No,” she said, squeezing his hand a little tighter, “I’m not mad. You at least told me this time, you didn’t just run.”

Jess brushed her cheek with his knuckles and her breath hitched a little. “True.”

“Jess,” she whispered, staring up at him.

He ran his knuckle down from her temple to her jaw and licked his lips in trepidation. “Rory.”

“We’re drunk.”

“So we are.”

“We shouldn’t do this while drunk. Besides, I’m…” it pained her to say this, “with Logan.”

He sighed and let go of her hand, nudging her hips a little so she’d move back. Rory stumbled at the suddenness of it all, immediately regretting that she somehow managed to keep a level head while tipsy. But, she did feel guilty; Logan was inside, none the wiser to her antics out here, and they’d been doing _so well_ together _._ Rory liked Logan. She liked him a lot, and she didn’t think about Jess when she was with him, usually. Tonight was just an outlier because Jess was actually here in person messing everything up, but she had no one to blame for that but herself.

“Let’s go back inside,” he said, pushing himself off the gate and leaving her to follow on her own.

The pub was rowdy now that everyone was done listening to the jazz singer and Rory and Jess returned to find shots on their table.

“And they return!” Logan said, sounding happy but slightly off-put by their disappearing act. “We’re doing shots, take a glass.”

Jess shook his head. “I’m good.”

“Ace?”

Rory closed her eyes, not wanting to look at Logan but she caved and did anyway. He was practically begging, and that look compounded with the guilt she was feeling worked against her. She grabbed her shot glass and raised it into the air to clink with Logan, Finn, Colin, Rosemary and Juliet. She downed it and relished in the feeling of the liquid burn, it helped to distract her from her emotions. She reached forward for Jess’ and took it without a word, her face screwing up at the double shot of sourness. Her throat felt raw, almost as if she’d just thrown up, and the buzz seemed to hit her almost immediately, silencing the more rational parts of her brain.

Now that the jazz singer had finished, the pub was playing regular music and Juliet and Rosemary were dancing together with Finn trying to make plans on how to get Rosemary to _finally_ go home with him. The group laughed and drank, though Jess stayed quiet and scooted in a little closer to Rory as the night went on. Rory felt emboldened by the alcohol and her senses seemed to sharpen when moved into her. She let her hand fall to his knee and she idly traced little designs it as she kept her eyes on Logan and laughed at whatever he was saying.

Jess grabbed Rory’s hand to remove it from his leg, but she turned her hand over in his and caught his fingers. She glanced at him from the corner of her eye with a little smile, not at all fazed by the rejection, before she let go. In all honesty, she had no idea what she was doing, flirting with another man while her boyfriend sat right next to her, but she didn’t feel like stopping. Could this even really be considering flirting if they touched all the time, anyway? He always kissed her, on the cheek and the forehead; she hugged him, they held hands sometimes, she even laid her head in his lap. Once upon time those actions all felt innocent, but the older they got the more things had started to shift and there was an under layer of _something_ indescribable, but it made her desire him in ways she’d never really let herself feel before.

Logan awakened a sexual fire in Rory more than Dean ever had, but if Jess was in the room, Rory knew which one she’d be looking at. She wondered what it would be like to be with him intimately. She’d been wondering for quite some time, but the way he looked at her and held her outside really drove the fantasy home tonight.

“Come with me to the bar?” She asked Jess, but he shook his head at her.

“I’m done for the night.”

Juliet piped up then, now sweaty from her dancing. “I’ll come with!”

“Me too,” Rosemary said.

Rory was slightly disappointed in the chosen company, but she didn’t let it show. The pub was spinning when she stood up, but she just giggled at it and shook Logan and Jess off when they both reached out to steady her. “I’m fine,” she slurred, turning to look at them over her shoulder with the wave of her hand before making her way over to the bar, only to be appraised by the bartender and told she was cut off for the night.

Surprisingly, she didn’t make a scene as she stopped back over to the table and threw herself in Jess’ lap. “He cut me off,” she whined, winding her arms around his neck. “I’m not that drunk.”

“You are pretty drunk,” Jess said, glancing over at Logan and Rory looked over at him too.

She grinned at her boyfriend and leaned into her best friends cheek, pressing herself firmly against him. “Hi.”

“Ace, come over here,” Logan encouraged with the swing of his head. “I’m sure it’ll be more comfortable.”

“No,” Rory said childishly, clinging onto Jess a little tighter. “Jess is very comfortable.”

“Rory…” Jess warned, and she leaned back to look at him.

“What?”

“Your boyfriend is pretty upset,” Jess muttered, only loud enough for her to hear.

Rory stared at him and then looked back at Logan. “Am I being a bad girlfriend?”

Jess shrugged. “Not to me.” He smirked and Rory hit him in the shoulder. “Ow! It was a joke.”

She slid off of him then and back into her seat next to Logan with a sloppy grin. “So, what’d I miss?”

 

**AGE TWENTY-THREE. AUGUST — ART GALA. NEW YORK**

Jess could tell that Rory was still having a hard time with the new Avery information.

Her eyes kept trailing over to Avery and Kimberly and she’d watched them for a moment until Jess caught her and then she’d look away, blushing. He wanted to tease her about it so badly, but he knew that’d just make things worse. Rory Gilmore had a crush and it was more than a little adorable. She just needed someone in her corner to tell her that it was okay.

He distracted her with food and alcohol, but he kept a close eye on the amount they both drank in fear of getting _too_ drunk and embarrassing the Ramesh’s.

“I think Logan’s here,” Rory said nervously, turning to face him. That hadn’t been what he’d expected her to say at all. “I think I saw him in the showroom…”

Jess took a sip of his whiskey and bit the inside of his lip. Rory’s crush on Avery didn’t worry him, but her residual feelings for her ex most certainly did. “What are you going to do?”

“I don’t know. Should I talk to him? Should I avoid him?”

“I can’t tell you what to do, Rory.”

She pouted at him. “Why not? You’re my boyfriend.”

A little jolt ran through him at the word. Their relationship was still new, and they hadn’t necessarily been referring to each other as anything except their names. Everyone who was important to them knew they were together by this point, so there was really no need to use labels or refer to each other with them, but now that she’d said it, it hit him in a whole new way. He was Rory Gilmore’s _boyfriend_.

“I thought you didn’t want me to be Dean,” he retorted drily, trying to keep on topic.

Rory wilted. “Ugh, I hate it when you’re right.”

“You have to do what’s right for you. Talk to him, avoid him, whichever, whatever. But _you_ have to make the decision, Rory, not me.” She whined at him and leaned her forehead against his collarbone. He instinctively wrapped her up in her arms and kissed the crown of her head. “It’s going to be fine.” He didn’t know if he believed it though.

“Okay,” Rory mumbled against his skin and he stirred at the contact. She pushed herself back. “I’m going to go talk to him. You’ll stay here?”

He nodded. “Yeah. I’ll be right here.”

Rory kissed him tenderly, his cheeks cupped in her hands. “I’ll be right back,” she said just before she went off to find her ex.

Jess glanced around the party room, now feeling awkward to be standing her alone. Matt was by the bar talking to some girl, and Chris and Lane were talking with another couple and laughing. They looked cute together with their drastic height difference and opposite skin tones and hair textures. Lane’s dress was something Mrs. Kim would definitely never approve of, but Jess thought she looked great in it. It was a pure, solid red and showed off more leg than he was accustomed seeing on her; the straps of the dress were thin so her shoulders were on display and she had her hair tied up in a sleek, high ponytail. She looked good, and Jess made a mental note to tell her so.

He leaned back against the wall and sighed, unsure of what to do now. He didn’t know how long Rory and Logan’s little talk would take, so he didn’t want to leave the area he promised he’d stay in just in case she came back within ten minutes or so, but he also had no one to talk to.

Finally, he spotted Ajmal across the room and he stood up a little straighter when they made eye contact. Ajmal excused himself from the small circle of people he’d been conversing with and made his way over to him.

“Jess, my boy!” He said, patting him firmly on the shoulder. They were never the type to do hugs. “You came after all.”

“I did,” Jess agreed. “Couldn’t pass up the chance to support your lovely wife.”

“Ah, yes, yes.” Ajmal laughed. “You always did like her more than me.”

Jess threw him a look. “You know that’s not true.”

Ajmal chucked. “So,” he said, changing the subject with ease, “Avery says you brought the wonderful Miss Gilmore with you tonight. Where is she?”

“She… went to talk to an old friend.”

“An old friend?” Ajmal repeated, thick eyebrows raised. “An ex?”

“How do you do that?”

His old teacher shrugged. “Pure talent. So, an ex?“

“Yeah.”

“The ex who proposed, I presume?”

“That’s the one,” Jess said, taking another sip of whiskey.

Ajmal hummed thoughtfully. “Well, I’m sure it will be fine.”

Jess shrugged. “I don’t know, maybe. He’s kind of a dick.”

“Biased opinion.”

Jess glared at him, but it quickly softened when he thought about it. “Yeah,” he admitted. “Maybe. But he has this ability to kind of force her into doing things that she doesn’t actually want to do, and this is their first time seeing each other since she turned him down.”

“Avery tells me that the two of you are _finally_ together.”

“Rory and I? Yeah.”

“I’m happy for you.”

“I’m happy for me, too.”

Ajmal gave him a wry, thin smile. “So, the relationship goes well? It’s healthy? Strong?”

Jess thought about it for a minute, hesitant to answer too quickly. He and Rory really hadn’t been together all that long, but it almost felt like they’d been together forever. “I think so, yeah,” he said, finally. “She’s been my best friend since I was sixteen and we’ve always been close… It doesn’t feel like much has changed, but I just get to love her openly now. It’s liberating.”

“Sounds to me like you have nothing to worry about in regards to this ex. The love is there, the two of you are working on it. You’re happy. Is she happy?”

“It seems that way.”

“Then trust that he no longer holds that power over her.”

 

**AGE TWENTY. OCTOBER — RORY’S BIRTHDAY. HARTFORD**

They stayed at the bar until closing, and Rory could feel herself sobering up. She was actually a bit thankful that the bartender had refused to serve her anymore alcohol, but she was a little upset that he’d kept on serving Logan and his friends. They were running around like wild children, clearly too drunk to drive. Juliet and Rosemary had hailed a cab and Finn, Colin and Robert ran off somewhere without her. In the end it was just her, Logan and Jess and there seemed to be some building animosity.

“Couldn’t help but notice the way you two were all over each other tonight,” Logan said, voice smooth as silk but Rory had learned when to pick up on the hurt by now.

Jess rolled his eyes and Rory bit her lip.

“Logan, it didn’t mean anything. We’re _always_ like that,” was her explanation, but Logan didn’t seem all that concerned with what she had to say. He took a step closer to Jess, and Rory reached out for Logan’s wrist but he evaded her grip. “Logan, don’t.”

“Stay out of this, Ace.”

“Logan!” Rory called after him, watching in horror as her boyfriend shoved her best friend.

“What?” He asked Jess. “Nothing to say?”

“Don’t touch me, man,” Jess cautioned him dangerously.

Logan pushed him back again, this time a little harder. “Yeah? What are you going to do about it?”

“Logan, please stop!” Rory cried, rushing forward to pull him back but he shook her off with ease. Her legs felt like jelly and her fingers were burning from the adrenaline.

“If you touch me again,” Jess growled, taking a step forward so that he was close up on his own terms, “you won’t like where it gets you.”

“You had your hands all over my girl tonight,” Logan said, sizing Jess up. “Tell me why I shouldn’t put you in your place?”

Jess laughed, harsh, loud, and short. “She’s not a possession, man.” He fell back and ran a hand through his hair. “Rory is perfectly capable of making her own decisions and we were _all_ drunk and we’re still _very_ drunk, so why don’t you get your ass home and sleep it off.”

“No.” It was a simple answer, adorned with yet another shove and Rory could feel the onslaught of a headache.

“Logan, please stop! Can’t you see that Jess doesn’t want to fight you?!”

Logan sneered at her. “Of course you would take his side. Are you two fucking behind my back?” He asked, keeping his eyes on hers.

“No! I would _never_ do that to you!”

“That’s not what it looked like to me.” Logan said easily. “You guys went outside, you sat in his lap. I noticed you holding his hand under the table. What am I supposed to think? You’re the one who came to _me_ with the ultimatum. You said _you_ were a relationship girl. I asked you if you were okay with open relationships and _you said no_ , but seems to me like that was a lie. Was it a lie, Rory?”

“No, it wasn’t a lie! That’s just the way Jess and I are,” Rory scrambled to explain, looking at Jess for help, but he kept his face impassive. “We’re affectionate, but we’re just _best friends_. You already know that about us! I’m not in love with Jess and he’s not in love with me.”

Logan turned back to Jess, curious. “That true?”

Jess didn’t react and his face didn’t change. “I don’t know. Maybe.”

That seemed to set Logan off, and he shoved Jess back again. “Don’t play games with me, man.”

“Guys!” Rory called out, feeling frustrated with the both of them now. “Can we please just go home? I’m tired!”

Neither of them listened to her. “You touch me again, and I’ll break your face.”

“Is that a threat, _Jack?_ ”

Jess stepped forward again, impassivity gone as he wore a deep scowl. “It’s a promise.”

Logan pushed Jess again, and she shrieked and squeezed her eyes shut once Jess started swinging. She heard the loud _pop!_ of Jess’ fist meeting Logan’s face, followed by Logan’s loud groan of pain. When she opened her eyes, Logan was on the ground with his nose bleeding freely and Jess was standing over top of him, breathing hard. She covered her mouth with her hand and blinked against the rush of tears building behind her eyes.

She didn’t know who to side with here.

Logan barely gave her anytime to respond before he was lunging at Jess from the ground with a howl. He gripped Jess’ shirt with his hands and slammed him up against the wall, screaming incoherent things. He let go to throw a punch and Rory watched in horror as it collided with the brick wall when Jess ducked and grabbed Logan by the arm to throw him back onto the ground.

“You have no idea when to stay down, do you?” Jess asked, and his voice was so cold that it scared her a bit.

She’d never seen Jess fight. Dean had told her about it a few times, and though she knew he was a scrappy kid from New York, she’d never thought that she’d get to see it up close one day. Logan moved to get up again, but Jess kicked him back down and Logan’s back slammed onto the pavement so hard that Rory winced. 

“Jess, stop!” Rory cried, barely able to get the words out as she rushed to Logan’s side. His arm was bleeding now in tandem with his face. He was practically covered in blood from the bleeding going on in his nose, and she wouldn’t have been surprised if it were broken, it did look a little crooked. “You’ve made your point!”

She was acute to the loud, harsh sounds of his breathing now and she stared up at him, convulsing with sobs.

“Please, just stop,” she begged, cradling Logan’s head in her lap.

Jess seemed to come back into focus then, his brow smoothened out and his eyes cleared up. He took a step back and rubbed a hand over his mouth as he assessed the damage, nodding in what looked like disbelief. She looked down at Logan, he was still conscious, his brown eyes a little hazy as he’d clearly given up the fight. Her heart swelled in love for him and she stroked his his forehead and placed small kisses on the crown of his head.

“Are you okay?” She asked him, sniffling through her tears. “You’re okay, right?”

“I’m fine,” Logan said a little thickly, pushing himself up out of her lap to spit out some of the blood that had got in his mouth. “I think I need to go to the hospital, though.”

“Do you need an ambulance?”

Logan shook his head. “No… It’s probably not that serious. We can take a cab to the clinic.”

She nodded dumbly, helping him up to his feet and fishing her phone out of her pocket to call for a taxi. When she looked back up, phone to her ear, she saw that Jess was already half way down the street. She closed her eyes, tears falling, as the taxi operator came on.

 

**AGE TWENTY-THREE. AUGUST — ART GALA. NEW YORK**

“Logan?” Rory asked the back of a slim, blond man in a crisp, dark suit. “Is that you?”

He turned to face her and she lost her breath for a moment when she took in those sparkling brown eyes. He smiled at her, big and wide, almost as if their last encounter hadn’t been him walking away. “Ace! Long time, no see.”

“Yeah,” she said, ducking her head to look down at her dress. “It’s definitely been a while.”

“How’ve you been? What are you doing here?”

“Oh, I was invited by a friend. Terra Ramesh is actually from Stars Hollow.”

“No kidding,” he said, disbelieving. “Small world.”

Rory swallowed against the lump in her throat. “Her daughter used to date Jess,” she said, clasping her hands behind her back so he wouldn’t see her nervous fiddling. “You remember Jess, don’t you?”

Logan’s face turned dark for a moment, but it cleared up quickly. “Your best friend,” he said easily. “Yeah. I remember him.”

Rory tried to smile, but she felt a little queasy. “Boyfriend now, actually.”

“Wow,” Logan drawled, his tone a mix between sarcasm and pure venom. “That was quick. You move on fast, Ace.”

“Logan, it’s been over a _year.”_ She didn’t know why she was shocked at his response, it was classic Huntzberger behaviour, but that most certainly didn’t mean that she had to put up with it. “I’m allowed to move on.”

“With the man who assaulted me.” He waved it away, but she could see the anger settling into the hard lines of his face. “It’s fine, Rory, really. I always knew you were into him. You denied it and denied it, but when you turned down my proposal, I knew. It’s just always gonna be good ol’ Jack. _He wrote a_ book, _Logan! He works in_ publishing _, Logan! He’s just so amazing and better than you in every way, Logan!_ ”

Rory gaped at him in disgust. “I never once acted like that! You did a lot of horrible things to Jess and I constantly took your side because I was your _girlfriend_ and I loved you. The only reason you proposed to me was because of the pregnancy scare. I said no because I didn’t _want_ to move to California with you and I most certainly did not _want_ to marry you because of a baby.”

“Well, then I guess it was a good thing it was a false positive, huh? Wouldn’t want you to ruin your dreams because of me! God forbid I just love you enough to want to marry you with or without a baby!”

“Logan, you’re being unfair.”

“Am I? Because I think you’re the one whose unfair, Rory. I gave you everything. I was a good, loyal boyfriend to you and you stabbed me in the back.”

“How?!” She cried, trying to keep her voice low so she didn’t cause a scene. “How did I stab you in the back? By loving you and supporting you? By cutting off contact with one of my best friends whom I _love?”_

 _“_ You _never_ wanted to be with me, Rory! You jumped from that guy who dumped you at your grandparents place right to me. I was the fall guy.”

“That’s not true! I did, I _did_ want to be with you!” They were starting to garner some attention now, and Rory could feel the eyes of strangers on her. She sniffled and wiped at her nose, careful not to ruin her makeup. “I can’t do this,” she said miserably, turning away from him to make her way back to Jess. She could hear Logan calling after her, but she walked a little faster, holding up the edge so she didn’t trip.

Thankfully, Jess was in the same place she’d left him and the tears started to fall once she caught sight of him.

“Rory?” He asked, rushing toward her. “Hey… what’s wrong? What happened? What’d he say to you?!”

“It doesn’t matter,” she said, careful not to get any makeup on his shirt.

“Of course it matters,” Jess said firmly, cupping her cheek in his hand. He wiped away some of her tears with his thumb so gently that she gripped onto him a little tighter. “He made you cry.”

She wiped at the remainder of her tears, smiling at her boyfriend a little. “How are you so good all the time?” She asked.

“I’m not,” he said, frowning. “I just hate people who hurt you.”

“It’s okay,” she said and meant it. “I’m feeling a little bit better already.”

“Do you want to go back upstairs? Maybe relax for a little bit? We can come back down when you’re feeling better.”

Rory thought it over before nodding. “Yeah,” she whispered. “That sounds nice.”

“Okay,” Jess said, placing a hand firmly on the middle of her back to guide her through the crowd.

 

**AGE TWENTY. OCTOBER — RORY’S BIRTHDAY. HARTFORD / STARS HOLLOW**

Jess slid to the ground, back hard against a brick wall as he stared out into an alleyway.

He didn’t know what he’d been thinking, if he’d even been thinking at all. Logan had pushed his buttons, but it’s not like he was the first person to do that. Maybe this was his punishment for not speaking up about he he really felt about Rory. It’d been months since his revelation that he was falling in love with her all over again, but she’d told him that she was _happy_ with that dick, so he hadn’t thought to say anything at the cafe. He wanted Rory to be happy. That’s what love was supposed to be.

Rory had said that she no longer felt that way about him, but tonight seemed to prove a little differently. Logan had been right beside her and yet she’d still chosen Jess at every opportunity she could find. That had to mean something, but then he’d gone an ruined it like he always did. Assaulting the boyfriend was a surefire way to lose the girl, no matter how into you she may have seemed. He should’ve known to just cut his losses. It’s what he did with everything else in life, but Rory Gilmore always had to be the fucking exception.

He sighed, hitting the back of his head repeatedly against the wall. Why did he always have to be such a fuck up? Maybe his mom was right. Maybe he _was_ doomed for failure. Jess pushed himself to stand back up, tired of hosting his own pity party, and grabbed his wallet from his pocket. Five dollars, great. That definitely wouldn’t get him back to Stars Hollow. His cellphone said it was close to three in the morning, and while this definitely wouldn’t have been the _first time_ he’d slept on the streets, he’d prefer not to.

Lane was definitely going to kill him for this, but figured it was worth a shot.

His phone rang twice before she picked up, voice groggy. _“Hello?”_

 _“_ Hey…” He said awkwardly.

 _“Jess, it’s almost three in the morning,”_ Lane whined, _“why are you calling me?!”_

“Please don’t kill me but I need a ride back to Stars Hollow.”

There was a pause on the other end and Jess was worried that she’d hung up, but then her voice came back on. _“Where are you?”_

“Hartford.”

_“Still?! Wow, you guys party late. Why can’t you take a cab?”_

“I don’t have enough money.”

Lane sighed, but she sounded more awake now. _“Okay, fine. Where are you?”_

It didn’t take her long to come get him all things considered. There was no one else on the roads, and he’d left the dark alleyway he’d been skulking out in so she could find him. He clambered into her van without saying a word, and they took off in silence though he could feel Lane glancing at him every so often until she broke down.

“Oh come on!” She said, keeping her eyes on the road. “Tell me what happened! I deserve to know! I drove out here at _three in the morning_ and I refuse to make the drive back without knowing the full story. I will park this band van, Sir. Don’t think I won’t!”

“I,” Jess paused, wincing at the idea of saying the words out loud, “kind of beat the shit out of Logan.”

 _“WHAT?!”_ Lane shrieked and Jess’ ear popped. _“YOU WHAT?!”_

“He kept pushing me! I told him if he put his hands on me one more time that I’d beat the shit out of him, and he did so I—“

“Yeah, beat the shit out of him, I got it! But Jess! Why did you do that?!”

“I just told you,” he deadpanned.

She glared at him before turning back to the road. “Not what I meant and you know it. Why was Logan pushing you in the first place?”

Jess groaned into his hands. “I don’t know,” he said, voice muffled, but he let his hands fall back into his lap. “Rory got drunk, like _super_ drunk and she was…” He trailed off with a sigh. There was no way he wanted to relive this.

“She was…?” Lane egged.

“She was all over me! She sat in my lap, she kept playing with my hands, her hand was on my knee. We almost kissed outside, I think, I don’t know…”

Lane shrugged. “You guys are always like that.”

“Yeah, but…” Jess searched for the words to explain, unable to come up with any. Curse his shitty drunk brain. “It’s just _different_ when we’re drunk.”

“Different how?”

“Lane, come on.”

“Hey!” She said, looking and sounding a little defensive. “You, Paris, and Rory are the naughty children. Mama raised _me_ right, in the eyes of the Lord. I am not a sinful child like all of you. I do not know what I’m supposed to take _different_ to mean. I assume it’s something sexual, but you’re going to have to explain it more.”

Jess pinched the bridge of his nose and stared out the window, knowing he couldn’t look at this innocent, tiny girl when he explained this. “It is sexual, yeah, but it’s like…” He sighed, feeling frustrated. “I get horny, okay?!”

Lane giggled and Jess shot her a glare which shut her up automatically. “Sorry, sorry. Rory’s told me the same about you, too.”

“That she gets horny around me?”

“Yep,” Lane said just as they made it into Stars Hollow. “Very horny. Paris almost convinced her into buying a Jess vibrator.”

“A what?”

“A Jess vibrator. A vibrator to use while thinking of Jess.”

He turned to look at her, shock evident. “You are _way_ too comfortable saying that for a child apparently _raised in the eyes of the Lord_. How often do you guys talk about this?”

“Only when drunk, I promise. I think Paris bought her the vibrator for her birthday, actually.”

Jess snorted. “I hope I’m drunk enough that I won’t remember any of this,” he said just as she parked outside the diner.

When he struggled with getting his seatbelt off, Lane leaned over to help him with a soft laugh. “I don’t think you have to worry about that, my friend. Need help getting inside?”

“Nah, nah,” he said, waving her concerns off. “I got it.” Jess opened the door and slipped out, stumbling a bit as he made it to the door and fumbled to find the key on top of the ledge. Lane sat watching him and he held up the key in triumph, grinning at her thumbs up. He ran back over to her and leaned against her door, smiling when she wound down the window. “Hey, Lane?”

“Yes, Jess?” She said playfully.

“I appreciate you. I’m gonna miss you when I move to Philly.”

She balked at him. “I’m sorry, you’re moving to _Philly?_ ”

He nodded. “Yeah, I wasn’t sure about it before but then… I assaulted Rich Dick and Rory probably hates me now and I hate my mom, _a lot._ I can’t stand seeing her in town, it makes me sick so… I just need to go, you know? Just get out of here for a while. “I wrote a book, I don’t think it’s any good but Ajmal likes it and wants me to shop it, so… I don’t know, it’s worth a shot and I’m no Huntzberger. All my dad’s got is a fucking hot dog cart on a beach and my mom didn’t give me shit except my name, so.”

He shrugged, fighting the urge to fall asleep right then and there, but he knew he needed to make it back inside.

“Plus, I’m never going to win Rory over,” he continued, feeling a little bad for word vomiting all over her, but he couldn’t stop himself. “No matter how attracted she is to me, she knows I’m not good enough, and I know I’m not good enough, and you know I’m not good enough. The whole town knows it. Even Luke knows it and her mom, oh _her mom, especially, knows it._ ” Jess laughed, hiccuping. “I hate myself, Lane. Did you know that? I just really, really fucking hate myself. There’s nothing good about me. My mom was right. I’m never going to amount to shit, I’m sure Philly will be a bust but there’s a possibility that it could work out in my favour just this _one time._ It’s a long shot but… I should try, right? Fight for something for once in my life?”

Lane got out of the van, careful not to knock him over and she wrapped a skinny arm around his back, tugging the key out of his hand as she guided him back to the diner with quiet, soothing little hushes. “Jess, you’re the strongest fighter I know,” she said, unlocking the door and pushing him through carefully. She guided him up the stairs to his bed, thankfully Luke wasn’t home, though he rarely ever was these days. “You’ve made it so far and you try _so hard_ and despite your mistakes, you are _so inherently good_. Even Mama sees it sometimes.”

Jess laughed as he fell back onto his bed. “Mrs. Kim does _not_ see it,” he argued as Lane wrestled off his shoes.

“Everyone sees it to a certain extent, Jess. It’s just that you don’t show it much.”

He stared up at the ceiling without a word.

“Are you going to be okay?”

“I don’t know. Probably.”

“You won’t like… hurt yourself, right?”

Jess snorted. “No.”

“You promise?” She sounded so timid and worried that Jess forced himself up to look at her.

“I promise.”

Lane shifted from foot to foot before she gave him a quick, but tight hug. “So, I’ll see you in the morning?”

“Probably the afternoon. I’m going to have a killer hangover.”

She smiled. “I’ll bring the aspirin.”


	9. Chapter 9

**Notes for the Chapter:**

> And the Gala continues but comes to a close this chapter.  
> Past!Jess is depressing, but also he really needed to go through this and I hope you liked his first meeting with the boys. 
> 
> As always, don't forget to leave me a comment on your thoughts and feels. I live for feedback.

**AGE TWENTY. NOVEMBER. PHILADELPHIA**

YOU HAVE ONE NEW VOICE MESSAGE.

TO PLAY THIS VOICE MESSAGE, PRESS ONE: **1**

 

_Hi, Jess…_

_It’s me, Rory._

_I just wanted to call and see how you’re doing. How’s Philly treating you? I heard it’s a pretty cool art scene out there now. I was reading it in the Times, and it looked sort of eclectic. A little forced and definitely posed, not candid by any means but still, they looked happy. I hope that you’re happy. Really, I do._

_I know we left things at a weird spot, but Logan’s doing fine after the fight and he said he has no interest in pressing charges, so that’s good. I wouldn’t want you to get a record because of me… I really screwed up, Jess. I always screw everything up when it comes to us. I just don’t know how to act when I’m around you, and I know I said I had it under control, but I don’t. I really don’t and maybe that’s why it’s a good thing you left, not that I’m happy about it. God, I am so not happy about it. I miss you with my entire being. Is that too dramatic to say? Well, I don’t care if it is. That’s how I feel._

_I love you, Jess. You’re my best friend next to Lane, and you’ve always been there. Do you know how weird it is to go into Luke’s and not see you? He even kept your handwriting for the specials board up. He’s an old softie. He misses you, too. He says you haven’t been taking his calls either, so I feel a little better knowing it’s not just me. Lane is shifty-eyed when I ask her, so I guess you’ve been talking to her, but I’m not mad. You should be talking to someone, even if it isn’t me._

_I’m sorry if you feel like you can’t talk to me, Jess._

_I know I messed up. I shouldn’t have asked you to come out with me that night, but I just wanted you there… Logan doesn’t like the fact that we’re friends, and I don’t really blame him after all that… I don’t know what to do it about it, but I guess it doesn’t matter since you won’t talk to me, anyway._

_I hope you come home or call me back soon. I miss you, and I’d love to hear all about Philly._

_Well, okay, that’s it. I’ve run out to things to say now, so… Bye._

_That sounds really lame right now, all things considered, but there it is—Goodbye._

 

WOULD YOU LIKE TO SAVE THIS VOICE MESSAGE?

TO SAVE PRESS POUND: **#**

 

**AGE TWENTY-THREE. AUGUST — ART GALA. NEW YORK**

They’d only been back in the room for around five minutes before Rory demanded that Jess go find Lane and the boys tell them where they were. He’d argued that they probably hadn’t even noticed their absence, but Rory was pretty adamant in keeping everyone int he loop. Jess left her with a bottle of water, the room service menu, and the television remote before making his way back down to the event, wading through a sea of people.

He found Matt first. His friend looked dejected at the bar, drinking alone as he pouted down into his glass.

“No luck tonight?” Jess asked, clasping him on the shoulder.

Matt hardly reacted, his dark eyes flickered toward Jess in recognition, but he was quickly back to drowning his sorrows. “I have nothing to offer these rich girls. They’re all screaming about Rory’s ex over there,” he mumbled, but then he stood up a little straighter and took Jess in head on. “Hey… does Rory even know he’s here?”

“Oh yeah,” Jess confirmed, gritting his teeth. “She knows.”

“You sound mad.”

“I am.”

“What’d he do?”

Jess sighed and rolled his shoulders back. “I don’t know all the details yet, but Rory went to talk to him and she came back to me crying. She’s in our hotel room right now taking some time to herself.”

“He made Rory _cry?_ And you didn’t kick his ass?”

Jess shrugged. “Rory wouldn’t want me to. Last time I did that we didn’t talk for a year.”

“Yeah…” Matt said, sounding a little wistful. “I remember that. That’s when we first met.”

“Yep.”

“Time flies.”

“It sure does.”

“Hey,” Matt said, brow crinkled as he looked past Jess and out into the crowd, “not to encourage any rash decision making, but I think your ex is trapped by Rory’s ex right now.”

“Wait, what?”

Jess turned to glance over his shoulder, catching a glimpse of Logan and Avery talking, wine glasses in hand. He turned around fully to get a better look, and noticed the way Avery was kind of folded into herself and smiling politely. Logan was conversing freely, gesticulating as he spoke, his eyes shining with mirth as he took Avery in, glancing at her from top to bottom every now and again.

“She looks uncomfortable.”

“Yeah,” Jess agreed, looking around for Kimberly. “Where’d her date go?”

Matt just shrugged. “Dunno. Maybe you should go rescue her?”

“No,” Jess shook his head, “bad idea. I hate him too much, it won’t end well.”

“Okay, _I’ll_ go save her then.”

Matt downed the rest of his drink in one gulp and made his way over to the two of them, a fake happy grin on his lips as he pretended to bump into Avery (or something like that, Jess assumed). Matt stuck his hand out for Logan to shake and Jess watched as Avery unfurled, her limbs loosening up in relief. She caught his eye from across the room and smiled, mouthing ‘ _Thank you’_ but he didn’t know what for, considering he hadn’t done anything.

He took in the scene one final time before setting off to find Lane and Chris.

Jess found them in the showroom looking among all the art and talking to the same couple he’d seen them with before.

“Jess!” Lane said, her face flushed red from the alcohol she’d been drinking. “Have you met Jamal and Sean? They’re from New York and they _love_ art. They go to art galleries together on dates, and they’ve admired Terra for so long. Isn’t that cool? That we grew up with an admired artist living in our town?! Tell me that’s not cool.”

“Sure, that’s cool. Very cool,” Jess said easily without really thinking about it. He raised his hand in silent greeting to Jamal and Sean before apologizing for needing to talk to Lane and Chris alone. When the couple was gone, Jess cut right to the chase. “Look, I’m just here to let you know that Rory and I are upstairs in our room. She’s not feeling well.”

“What?” Lane asked, looking worried. “Is she sick? Does she need me? I brought her all her favourite medicines, and a can of soup just in case.”

Jess quirked a brow.

“I’m a very good friend!” Lane defended herself, tucking herself into Chris’ side a little bit as a shield.

“I didn’t even say anything _._ Besides, I already know you and Rory are weird.”

“You’re judging me with your judgy eyes! Tell him, Chris.”

Chris smiled a little sheepishly. “You do have those judgy eyes going on, man.”

Jess rolled his eyes to the ceiling. “Whatever. I just came to let you know where we are in case you came looking for us.”

“But, Rory’s fine, right?” Lane asked.

He fought the urge to sigh at her constant mothering. “Yes, Lane. She’s fine. I’ve got it under control. I’m sure she’ll tell you about what happened later. Now, I’m going back upstairs. If you need me, call my cell or the room, whichever, whatever. Enjoy the Gala.”

Once he made it out of the showroom, he had a difficulty of pushing his way through the crowd of people gathered in the party room. He could hear someone walking behind him, but he wasn’t paying much attention until they called out his name when he finally made it out.

Jess turned to see Avery wiggling her way out of a large group of people, her face set up in frustration as she stumbled a bit in her heels. He stepped forward to steady her, but she managed it on her own.

“Hey,” she said, a little breathlessly. “I forgot that you walk fast.”

“You’ve always managed to keep up before.”

Avery glanced down at her shoes and stuck a foot up for emphasis, rotating her ankles. “Not with these babies on.”

He smirked. “So, what’s up?”

“You were right—he’s a jerk.”

“Logan?”

She nodded, smiling a little. “Logan.”

“What’d he do?”

“I’d heard that a man in the showroom made one of our guests cry, so I went to check it out and I saw Rory rushing away and Logan just standing there, calling after her. I left it alone but stayed close, just in case. Nothing happened for a while so I figured I’d go and mingle, and then he found me, eventually. We got to talking, he introduced himself, said he was here looking for artwork to buy for his sister or something—a friend of his recommended my mom’s work. He seemed nice, our conversation was easy, effortless, really, but I don’t know. I guess I said something he liked and then he started advancing, and you know me, not very good with the whole _advancements_ thing.”

“I do know that about you, yep.”

“It was mainly just some gross comments about wanting to hook up, some weird _where are you from, you look exotic_ kind of questions, but then…“ Avery licked her lips and directed her eyes toward the floor. She seemed oddly nervous, and it made the hairs on the back of his neck stand up. Something was off.

“Avery, what’s going on?”

She looked at him, her cheeks sucked in a little bit before she said. “Do you mind if I talk to Rory?”

“Uh,” he said, a little taken aback by the question. “No? I’m not her keeper or anything.”

“Well, I know that. It’s just… Logan said something and I think she should hear it from me first instead of from me telling you and then you telling her. It gets messy with he-said, she-saids.”

Jess nodded in agreement, not able to find anything to argue with. “Right.”

“So, you don’t mind?’

“Not at all.”

The tension in her shoulders seemed to melt away and she gave him a real smile. “Great, then lead the way.”

“Wait, I thought you wanted to do this alone?” He asked, wrinkling up his nose. Jess couldn’t figure out for the life of him what Logan could’ve said to her, and he honestly wasn’t certain if he even wanted to know.

“No, I just want to tell her myself, but there’s no reason why you can’t be there—unless she doesn’t want you there, but that’s up to her, not me.” She leaned forward to press the up button and folded her hands in front of her.

“Fair enough.” Jess nibbled at his top lip, looking back at the party room. “Hey, uh… Where was Kimberly after the whole Logan thing?”

“Oh, she went up to her room after about two hours. Early flight back and all.”

“You met her in Boston, I assume?”

“Mhm. She works in the lab with me. She’s nice.”

He felt a little awkward talking about this, even though he had been the one to bring it up. It wasn’t the first time he’d seen his ex with someone else, but it wasn’t any easier now than it had been back then. “She seemed nice—not that I talked to her much.”

Avery hummed. “Yeah.”

The elevator came then and Jess thanked a long list of deities. He gestured for her to go in first before he followed and hitting the number six on the panel. They rode up in silence, the air so thick that Jess could hardly breathe. The combination of recent events had him on edge. He put on a brave face but it was hard being around Avery while in a new relationship, and he knew Avery and Rory were friends now but that didn’t make things any easier on him.

 

**AGE TWENTY. NOVEMBER. PHILADELPHIA**

He didn’t know why he came out here.

Ajmal had been wrong about him. He wasn’t talented and he certainly wasn’t made for networking. Social interactions exhausted him, and he didn’t know how to bite back his sarcasm. Ajmal’s contact had been a stuffy man in a suit who talked about marketing and big numbers. Jess just couldn’t relate to him at all, not even when he took him to the office and showed him around. All he could think was that he’d shoot himself if he worked here. Everyone looked like a fucking clone with dead eyes, and this definitely _was not_ going to be his bread and butter.

 _Okay, but you need a job_ , the intelligent part of his brain said, but sarcastic, pretentious Jess always won out in the end. How the fuck did he think he was too good for a job paying more than minimum wage when he didn’t even have a college degree? Who did he really think he was?

Jess groaned, trying to sink down into the firm mattress of his hotel bed. He pulled the blankets up over his head as he recalled his own very stupid decision to turn the job down. It was just like Liz said, he was a bum. He was a bum who was never going to amount to anything. Even Ajmal had called him, sounding disappointed. Jess couldn’t handle it so he’d put his phone on silent and avoided every single call that came through, only choosing to call Lane back sometimes.

He rubbed a hand over his face, trying to ignore the stiff, aching feeling in his back. It’d been two days since he’d turned down the job (after two weeks of negotiating and talking) and he hadn’t left his room at all. The hotel was kind of fancy, with free breakfast, internet, and television. He felt guilty staying in a place so nice, but Luke had been adamant about paying for it all so that Jess didn’t put a dent in his savings.

Going for a walk seemed like a good idea, the fresh air would probably make him feel a little bit better, but he couldn’t bring himself to get up. There was no point to anything anymore. Philadelphia had been a bust, and he needed time to wallow, even if he was getting a little sick of it now.

Jess forced himself up, throwing the covers back with a sigh to grab his phone off the floor. There was a new missed call from Rory, but she hadn’t left a message this time. He’d listened to her old one over ten times by now, trying his best to dissect her rambling in a way that actually made a bit of sense. Not to mention he just loved the sound of her voice. It was all so stupid, honestly. He’d left Stars Hollow for a variety of reasons, Rory included, and yet he still yearned for her as if nothing had happened between them at all.

He wanted to see her so badly he thought his heart was going to physically break. His mind wouldn’t stop reminding him that before he’d screwed everything up, Rory had wanted to move in with him. He wondered what that would be like, he wondered if the close proximity and unavoidable domesticity would force them into confronting their feelings for one another. It was better that it never happened in the end.

Jess shook his head, trying to clear his thoughts as his phone screen came back into focus. Luke had called twice, but he scrolled past it, unwilling to think about his pseudo-father and the amount of love and support he’d left behind in Stars Hollow. Just beneath Luke’s name was Ajmal’s contact—Greg. He’d called early in the morning and left a message. Jess bit the inside of his lip, took a deep breath, and played the voicemail on speaker.

_“Hello, Mr. Mariano. I’m sorry to be calling you so early in the morning, but Ajmal told me you were still in the city and I have a proposition for you. If you wouldn’t mind calling me back at the office whenever you have time, that would be greatly appreciated. You can reach me at—“_

Jess leapt out of bed at Greg started to recite the number, grabbing his notebook and a pen and jotting it down quickly. He saved the message and listened to it again to ensure the number he’d copied was right. When he was sure he’d got it down properly, he dialled the number back, bouncing his knee as the phone rang.

_“Hello, Gregory Wolla speaking.”_

“Hey, Greg,” Jess said, his tongue felt thick and heavy in his mouth. “It’s Jess Mariano.”

_“Ah, yes! How are you?”_

Jess twisted his lip to the side so he could bite at the inside skin of his cheek. “I’m good. How are you?”

 _“Exhausted, really.”_ Greg sighed, sounding weary. _“Work has been hectic.”_

“Oh. I’m… sorry?” He offered, still not quite knowing how to talk to men in suits. His uncle owned a _diner_ , and Andrew was a quirky man in a quirk town, Jess had never dealt with intimidating professionals before. The closest he’d ever come was Richard Gilmore, but even conversing with Rory’s grandfather seemed easier than this.

_“It’s fine, it’s fine. Anyway, I called you earlier because I have a proposition for you. Now, before you say anything, I just want you to know that it’s not for HBG, it’s actually for a much smaller company, one of my affiliates—Truncheon Books.”_

Jess wasn’t sure what to think of this. Truncheon didn’t sound like a company that’d been associated with Hatchett Book Group, but he supposed he really didn’t know all that much about the industry, anyway.

_“It’s only been up and running for about a year or two now, but they’re doing some great stuff. It’s run by a bunch of young guys, all around your age, and they’re more focused on the indie niche. I think you might fit in there.”_

“And they’re hiring?”

_“Two of their guys just left, they came over to Hatchett, actually. So, Truncheon is in need of a few replacements.”_

Jess inhaled sharply, but exhaled quietly. Maybe Philadelphia wasn’t so bad after all. “When can I meet them?”

_“Tonight would be best, if you don’t mind. Casual setting. Their favourite bar is just around the corner from the hotel you’re staying yet. I’ve already put the idea of you into their heads, they seem intrigued by you. I think it could work out.”_

“Wow,” Jess said, feeling a little dumbstruck. “Uh, thanks for thinking of me.”

_“Networking is the key to everything in this industry, Jess. I hope things turn out well for you.”_

 

**AGE TWENTY-THREE. AUGUST — ART GALA. NEW YORK**

Rory could hear Jess and Avery talking outside the door, but she had no idea what they were talking about.

She was laying in bed, room service menu fully circled with all the things she wanted but felt bad ordering considering this was not going to be on _her_ tab, so she’d been waiting for Jess to make his way back but he’d taken longer than she thought he would. She found a fancy vending machine on her floor filled with snacks and drinks, so she’d grabbed herself a bag of chips and a coke before getting cozy in bed with a bad movie. Her encounter with Logan had left her feeling a bit more fragile than she’d liked and she was determined to get over it before the night was over.

Finally, Jess and Avery quieted down and Jess slipped his card into the slot. Rory kept her eyes on the television, not wanting to seem too eager, but she couldn’t help raking her eyes over him appreciatively. Her boyfriend cleaned up well. She liked the way he didn’t fight her on the tie that matched her dress, and she especially liked how good he looked in a crisp white shirt, dark grey blazer and matching slacks. His shoes had been borrowed from Chris, they were black oxfords that looked really good on his feet.

When her eyes finally met his, she found him smirking at her. “You gettin’ ahead of yourself there, Gilmore?”

“No,” she said flirtatiously, forgetting all about the fact that she’d heard Avery with him outside the door, “I’m going along at just the right speed.”

He grinned, leaning onto the mattress with his palms to kiss her. She hummed appreciatively, but pouted when he broke it too soon.

“You have a visitor,” he said seriously, and suddenly her brain snapped back into motion.

“Oh, right!” She said, hitting her forehead with the heel of her hand. “I knew I heard Avery with you out there. What’s going on?”

“Logan cornered her.”

Rory felt her stomach drop. “He did?” God, poor Avery.

“Yeah. Matt saved her, but not before Logan told her something.”

“What?”

Jess shrugged at her with the shake of his head. “I don’t know, Babe. She said she wanted to tell you herself.”

Rory tried to shake off the happy little chill that came with Jess calling her _Babe_ and focus on the current issue at hand. “Why is she waiting outside then?”

“She didn’t know if you’d want a visitor.”

“Wow,” Rory breathed. “That girl is very considerate.”

“I like to joke that she’s an empath.”

Rory smiled, leaning in to kiss him again. “Nerd.”

He cupped her cheek as he kissed her back, sipping at her lips a little longer than he had just a moment ago. When he broke away, he leaned his forehead against hers. “You okay with a visitor? Feeling up to it?”

“Yeah.” She wasn’t really feeling up to it at all, but her curiosity outweighed her desire to be alone with her boyfriend at the moment. “Bring her in.”

Jess kissed her again, but it was more like a peck than anything, before he pushed himself off the bed and back to the door. He opened it and let Avery in, and Rory bit her lip in anticipation, trying to ignore the little jolt in her tummy.

“Hi,” Avery said with a smile, immediately finding a place to sit at the edge of the bed. She pulled her long dress up to show off a bit of her bare, smooth leg so she could tuck it freely underneath her thigh. “How are you feeling?”

“Better, now. Did Jess tell you…?”

“No, no.” Avery shook her hand, a single hand up in the rejection of that idea. “I saw you crying, so I kept an eye on Logan in case he tried to go after you and start something—or _more_ somethings.”

Rory looked down at the bag of chips on her lap, cheeks hot in her embarrassment. She’d hoped that no one she knew (other than Jess) had seen her cry at the hands of Logan Huntzberger. Her ex had never done well with being respectful of her feelings in public anyhow, and now that they were no longer together it seemed like he cared even less.

“I’m sorry. This is your mother’s event and Logan and I caused a scene…” Rory sighed, forcing herself to sit up a little straighter so Avery could know she was serious about this. “I want you to know that was _not_ my intention.”

“Rory, you have nothing to apologize for,” Avery said, sounding a little sad; Rory really hoped that it wasn’t pity she was hearing. “Logan Huntzberger is _definitely_ a piece of work. Which, is pretty much why I’m up here, anyway.”

Rory bit her lip, trying to prepare herself for whatever horrible news was coming next. “Yeah, Jess alluded to something…” She looked over to him sitting in the arm chair by the closet, his gaze flickering between them and the television, almost as if he were trying to give them privacy. Rory did spot a ghost of a smile when he looked her way though.

“I don’t know how true this is, or if he was just saying it so that I would tell you and it’d bug you out… but he said he was thinking of going back to the Huntzberger family business. Something about California not being all it’s cracked up to be.”

“Oh,” Rory said, blinking hard as her brain tried to take in this new information. “That’s… good for him, I guess…”

She felt a little odd at this news, though she mostly felt foolish for having once believed that Logan could break free of his ball and chain to live the kind of life he deemed worthy. This news should not have been shocking to her in the slightest, but yet it felt like a knife had been driven through her heart. She remembered all their late night talks, how she’d encouraged him to leave the Huntzberger empire behind if he really wasn’t happy being apart of it. Rory linked her fingers together, remembering the way he’d grab her hand and say he couldn’t find the courage to escape it all without her. She’d considered it all just flowery words at the time, but maybe he hadn’t been lying at all.

“He also said that his first line of business would be to buy out some papers on the east coast. He specifically name dropped Metro.”

And now she felt sick.

“He’s lying,” Rory said quickly, feeling a little panicky, “he can’t just buy Metro because I work there! That’s unethical _and_ disgusting! The company is doing just fine on it’s own, more than fine, really. It’s thriving!”

Avery leaned forward to grab her hand, the same way she did when they’d been in the coffee shop. “Hey,” she said soothingly, “it’s going to be okay. Who knows if he even meant it, right? But I just figured that if he did, you’d like a warning.”

Rory squeezed her hand back this time, relishing in the comfort of it.

“He seems like he really knows how to get under people’s skin,” Avery continued, frowning. “I think he was counting on me to tell you this, maybe so you’d go and tell your boss and seem paranoid or something. He seems crafty that way but I could be misreading him. Am I?”

“I don’t know,” Rory said, shrugging. “I felt like I knew him. I was with him for almost three years, but …” She shrugged again. “Logan _can_ be vindictive, I guess, and he has a tendency to treat people badly if he thinks they’re beneath him but he’s truly never been anything but kind to me, even in his most unkind of moments. If he said something about trying to buy Metro, then it probably is true, and it’s just a matter of time until I hear about it.”

“I’m sorry.”

Rory shook her head, trying to force a smile to her face. She really hadn’t planned on feeling sad or dejected while on vacation. “It’s not your fault. Thank you for telling me, otherwise I might’ve been blindsided by it.“

“That was my fear.”

“There is the possibility that it was all talk though, right?” Jess asked from his side of the room.

Avery let go of Rory’s hand then so she could get a better look at Jess. “I guess so, yeah.” She turned back to Rory. “What do you think?”

“Well,” Rory said, pinching her bottom lip between her thumb and index finger, “his dad always had him stationed out in London, so I _do_ think if he goes back there, that Mitchum will put him exactly where he wanted him to begin with. But, there’s also the possibility that Mitchum’s feelings and plans have changed. There’s really no way to know what’s going to happen…”

“So,” Jess got up from his chair and made his way over to the bed, “it’s better not to stress about it, right?”

She knew that was easier said than done, and she knew that Jess knew it as well, but she appreciated the way he tried to comfort her in distress. “Yeah,” she agreed, though not really meaning it, but she was going to try.

He wrapped an arm around her shoulder and placed a small kiss to her temple, and she blushed at his open show of affection. Was this weird for Avery to see? If the roles were reversed, how would Rory feel? She wanted to shy away from him out of respect for the gorgeous woman in front of her, but she couldn’t help feeling safe with Jess wrapped around her like this.

“Thanks again for telling me, Avery,” Rory said, hoping that she sounded as genuine in her appreciation as she felt.

Avery beamed at her, dark eyes alight. “You’re welcome. I just wanted you to know, as I said, just in case he was serious.”

“I really appreciate it.”

“I’m glad,” Avery said, getting up from the bed and fixing the skirt of her dress. “I should probably get back down there, it’s getting late and Mom wants to give a _Thank You_ speech to everyone who came. I don’t want to miss it.”

Rory looked at Jess, eyebrows raised, before she turned back to Avery. “We’ll come, too.”

“Oh,” Avery looked between them, brows drawn tightly together, “Are you sure? Logan might still be down there.”

“I’m sure he is,” Rory said with a small shrug, trying not to care. “But I’ve still got my dress on, Jess is still put together, and I’m not quite tired enough for sleep. Your mom was nice enough to invite us and put us up here, so the least we could do is be there for the end, right?” She directed that question at Jess, holding her gaze on his again.

“Sure,” he said easily, unwrapping his arm from her shoulders to stand up. He held his hand out to her and she moved her bag of chips onto the bedside table before sliding her palm into Jess’ own.

 

**AGE TWENTY. NOVEMBER. PHILADELPHIA**

The bar was loud and distracting, which didn’t do much to help Jess’ mood or keep his attention on his book.

He was anxious to meet these Truncheon guys and see if he could _finally_ make something of himself out here. His mind was racing with old memories, mainly his talk with Jimmy back in California when he’d begged his father to let him stay. He hadn’t known what he was going to do with his life then, and he’d been terrified of the whole ordeal, and not much had changed now. Jimmy was not what Jess would call father material, but somehow he’d managed to make Jess feel a little bit better in the end. They still weren’t close, but at least Jess knew where he came from… If he failed here today, he knew he had one parent who’d manage to make something of himself, even if it wasn’t a line of work that Jess particularly saw himself in.

“You want another?” The bartender asked him, pointing to his empty beer glass. She was a petite woman, her pretty face framed by long dark hair. Her skin was a tawny brown colour that seemed just a few shades lighter than Avery’s, but he could tell by the cut of her tank top that it was a summer tan that’d yet to fade.

“No, I’m okay.”

She studied him and then leaned onto the counter. “What’s your deal? I’ve never seen a guy come into a bar with a _book_. Well, not entirely true, my friends are book nerds but you seem to trump them a little bit. They just gush over the books and talk about nerd stuff like the finish—matte or gloss,” she rolled her eyes, “or sometimes they get mad that the printer fucked up.”

Jess smirked. “I have a feeling I’ll be meeting your friends in a minute then, if they are who I think they are.”

The bartender leaned back then, taking him in. “Ohhh,” she said, nodding, “you’re Brandon and Sean’s replacement. Chris told me to look out for you, I must’ve spaced.”

“I don’t even know if I have the job yet.”

She giggled at him almost as if he’d said something funny. “Trust me, you’ve got the job. One look at you and I can see you fitting right on in.” She didn’t give him the opportunity to respond as she moved to the other side of the bar, another beer glass in her hand. When she came back, she placed it down in front of him. “It’s on the house,” she said with a rather dramatic wink.

Jess watched her move around the bar, appreciating her fluidity. She moved with a certain kind of grace he found attractive, and her body looked lithe and nimble like a dancers. He took a sip of his beer and tried to go back to his book, but he found her taking more of his attention than he thought she would.

“Hey,” the bartender whispered to him after a while, leaning in close. “They’re here.” She nodded toward a booth somewhere off to the side and he witnessed three guys being led to a booth by a waitress. “Go head on over, and good luck—not that you’ll need it.”

“You seem to have a lot of confidence in me for a girl who doesn’t even know me,” Jess teased.

She smiled playfully at him. “I know my friends and you just seem like their type. If I’m wrong, I’ll buy you dinner.”

Jess laughed at her flirting, pushing himself off the bar stool. “And if you’re right?”

“Then you’ll buy _me_ dinner.”

“Huh.” He kind of liked how forward this girl was, it was a nice change from Rory’s constant running. In a way, he’d almost forgotten what it felt like to be so obviously desired.

“Now, go! Blow them away, mystery man.“

Jess couldn’t think of anything to say, so he just have her a half smile, gathered up his things and made his way over to the booth the bartender had pointed at. The three guys were talking amongst themselves, but they stopped when Jess made himself known. One of them, a tall black guy with a thick head of fluffy curls, stood up to shake his hand.

“You’re Jess?”

“That would be me.”

The guy nodded. “Nice to meet you. I’m Chris, and this is Matt and Austin,” he said, gesturing to the other two guys in the booth.

Matt seemed to be the white guy; he was kind of wholesome looking with a sweater over a button up shirt, and a mop of brown hair with brown eyes to match. Austin was East Asian and kind of edgy with a muted aesthetic, two small spacers in his ears, and an eyebrow piercing. His hair was cropped short on the sides, but it was long on top. They both greeted him with the single raise of their hands.

“Nice to meet you.”

“Come,” Chris said, getting back into the booth and gesturing across from him. “Sit.”

Jess nodded once with the jerk of his head before sliding into the free space beside Austin.

“So, Greg says you wrote a book,” Matt said, jumping right into things.

“Uh, yeah,” Jess confirmed, shrugging a bit. “I brought it with me, actually.” He held up his red notebook.

Austin laughed at the sight of it, and Jess started to panic, though he kept it cool on the outside. Hachett really hadn’t minded seeing it on paper, but maybe these guys were more technology buffs. He was regretting not taking up Greg’s offer to type it up.

“I like this dude,” Austin said, and Jess relaxed immediately. “He’s straight up analogue. A manuscript written by hand is fucking _metal._ ”

Chris rolled his eyes, but he smiled all the same. “Ignore him. We’re professionals here, I swear. Would you mind if we took a look at your manuscript?”

Jess simply handed the notebook over. He was nervous about it, but he forced himself to get over it. The Subsect was _not_ what he wanted it to be in the slightest, but he’d done his best to rework it with Ajmal into something that he could shop. Writing it out by hand had been tedious, but it was definitely the only way he could do it without a laptop. Luke was still more anti-technology than Jess would probably ever be.

He tried not to get too nervous as Chris flipped through it, brown eyes skimming the pages.

“So, Jess,” Matt said with a grin. “Where are you from?”

“New York, originally. Moved to a small town in Connecticut when I was sixteen.”

“Ew, why?” Matt asked, wrinkling up his nose. “That’s the state of rich yuppies and nutmeggers.”

Austin snorted. “You’re literally _from_ Connecticut, Matt.”

“I know! Hence why I _know_ it’s filled with yuppies and nutmeggers.”

Jess smirked, thinking of Stars Hollow and Hartford. “You’re not wrong.”

“See! He knows. Literally everyone from Connecticut is _ashamed_ to be from Connecticut, so when people ask where you’re from you say _near New York_ because that’s significantly less embarrassing. Granted, no one in Connecticut knows a thing about New York, but they like to pretend.”

He wanted to bring up Rory, and how she referred to New York as _the big apple_ and how ridiculously touristy she looked in the city, but he also wasn’t the type to just start giving out personal anecdotes. He barely knew these guys, but somehow he felt comfortable already.

He’d even managed to forget that Chris was reading some of his most personal inner thoughts until he closed the notebook with a look of awe. “Holy shit dude,” he said, looking at Jess in a whole new light; that look reminded him of Ajmal when he’d first read some of Jess’ work, and it still made him a bit uncomfortable. “Your writing is _so raw._ Who are your biggest influences?”

“Hemingway. Kerouac. Bukowski. Maybe some Austen in there, too, I don’t know.”

Chris nodded. “I can see them, but not in a rip off way. It seems fresh, original.”

Matt was scanning through the notebook now, his face made up in a _Wow, very impressive_ sort of look before he handed it off to Austin.

“It’s just a short novel, it’s nothing special,” Jess said, fighting the blush rising to his cheeks. It was rare for anyone to make him blush, yet somehow these guys had managed it in under twenty minutes.

“We’d love to have you.”

Jess stared at Chris incredulously. “You don’t even know me.”

Matt shrugged. “So, we’ll get to know you. Do you have any publishing experience?”

“No.”

Austin laughed. “He’s such a sharp shooter. I don’t think I’ve ever met someone so straight forward in my entire life.”

“I don’t see a point in lying to you about my experience,” Jess said, glancing at Austin out of the corner of his eye. “All I know is that I’m twenty, I need a job, and I need to figure out what the hell I’m going to do with my life. If you’re serious about helping me, great, but if you’re just pulling my leg—“

“Jess, man,” Chris cut him off with the shake of his head and a smile. “Your writing is _good_ , and Greg only said nice things about you. He talked you up massively, and I have to say I don’t think any of us feel disappointed. I get it, we don’t really know you, but you’re walking around in a bar with the fucking _Odyssey_ in your hand like it’s no big deal. Now, you could be faking your love for books but somehow I doubt it.”

“There’s an authenticity about you that’s hard to find,” Matt said with a warm smile. “And trust me, we’re picky.”

“The fact that Austin liked you on sight says enough.”

Austin shrugged, his palms open and pointed up to the ceiling. “What can I say? I have a very strong fake radar. It’s stronger than my gaydar—which is impeccable.” He paused for a minute, narrowing his eyes at Jess. “You’re not homophobic are you? I’m not getting that vibe, but I have to make sure.”

Jess shook his head. “Nope.”

“Okay, good. Because two of us at this table are very open and proud gay and bisexual men.”

“Shut up,” Chris said easily, though he didn’t look annoyed. “He doesn’t need to know all of that right now, it’s not like he’ll be living with us.”

“He might have to,” Matt said thoughtfully, looking between everyone at the table. “He’s not from here.”

Chris took that information in for a few beats before he asked, “Do you have a place of residence, Jess?”

“No, but, I can find my own place. You guys don’t need to put me up.” The last thing he needed was to owe more people. “I can take care of myself. Always have, always will.”

“Where are you staying now?”

“A hotel.”

Matt tsked. “In center city? That shit is expensive.”

Jess licked his lower lip, not knowing what to say. Did he tell them that his uncle was paying for it? That seemed too personal, so he decided to be vague. “I have a lot of money saved up, I can get my own place so long as I have a job.”

“We don’t pay much, honestly. You’d probably make over minimum wage since there is a possibility you’ll be taking on two jobs.”

“Two?”

Austin nodded. “Yeah. Brandon _and_ Sean left, and we don’t have enough money to hire two replacements, so your responsibilities would include two jobs. We’re looking for a line editor and someone to work the bookshop floor.”

“I’ve worked in a bookshop for about three and a half years, actually,” Jess said, suddenly feeling a lot better about this whole thing. The responsibilities at HBG seemed too far out of his realm. A lot of it had to do with marketing and wearing a suit and talking about things that he really didn’t care about. All he really wanted to do was read books and get paid for it, and line editing seemed right up his alley for that.

“Really?” Matt asked, sounding excited. “That’s great! So you understand book organizing and all of that?”

“He’s just excited because he hates that part of the job,” Chris explained with a pointed look.

“Hey, man! I like things organized, I have a very specific system that you and Austin just don’t seem to respect. I need someone on my side!”

“Oh, boohoo, I moved _one_ book and you freak out.”

“It throws the whole system off!”

“You’re such a baby,” Austin chimed in.

Matt huffed, crossing his arms over his chest. “Poetry and novels _do not go together!_ It’s fucking common sense, okay?! Our customers will get confused! And why can’t we ever keep the storefront clean, anyway? Do you know what our customers must think?”

Jess just watched them banter, smirking quietly to himself as he fought to stay quiet.

Yeah, he could definitely fit in here.

 

**AGE TWENTY-THREE. AUGUST — ART GALA. NEW YORK**

Rory was kind of excited to be back at the Gala, despite Logan’s presence hovering around. Jess was careful not to leave her side for too long, and he kept his hand firmly wrapped around her waist when they engaged with other groups and couples. She’d caught Logan’s eye over by one of Terra’s paintings, he stared at her a little sombrely, but Rory kept her chin held high before she broke their gaze. She refused to let him ruin her night anymore than he’d already had.

Many people seemed to be putting out bids for Terra’s artwork, and even Rory considered fighting for a beautiful portrait of an elephant painted in various shades of blues and silvers, but Jess had convinced her not to for a reason he couldn’t quite explain. Rory kept her eyes on him out of curiosity, smiling as he placed his own bid down when he thought she wasn’t looking.

Jess didn’t do big, grand gestures like Logan did. His romanticism was quiet and subdued, but she liked that. Dean had been too cheesy; it’d been nice for her first boyfriend, but his gifts always came with some sort of emotional price. Logan had been too flashy; she’d appreciated the Birken bag, the rocket,, the candle lit dinners on the rooftop, but he’d never listened when she said that wasn’t what she wanted.

Even if Jess didn’t wind up winning the bid, the fact that he wanted to buy it for her made her feel giddy enough.

Terra brought the event to an end with a beautiful speech, and Jess kept Rory at his side via her own request when it looked as if Logan was hovering around to talk to her again. Her ex gave her a final look, wistful and a little bittersweet before he took his leave, and Rory did her best to let that be the final chapter of Logan Huntzberger. No matter what happened with Metro, she knew she couldn’t allow him to dictate her life any more than he already had.

Rory slipped her hand into Jess’ and gave him a thankful kiss for staying by her side.

The Philly group made their way back up to the sixth floor, though they congregated in Jess and Rory’s room just as they had earlier. They celebrated the end of their fun night by opening the bottle of champagne that Avery had brought to them earlier and lounged around listening to some music they found on a TV-slash-radio station.

Rory’s stomach grumbled and she placed a hand on her belly, looking up at Jess with a pout. They’d collapsed on the bed, still in their classy attire, though Jess’ tie was hanging loose around his neck.

“Feed me.”

He laughed at her and placed a small, chaste kiss to her cheek. “I was wondering when you were going to start complaining.”

“The finger food was delicious and all, but finger food _cannot_ hold over a Gilmore.”

“I expected as much.”

She tucked her face into his neck. “So, food?”

“Sure. New York’s got some cool places open all night.”

Rory squealed, not having even thought about the possibility of going out into the city. “I was just going to suggest room service, but I would kill for a twenty-four diner! You guys in?” She asked Lane, Chris and Matt, but they all just shook their heads at her.

“Nah, I’m beat,” Lane complained. “Who knew standing up for hours and schmoozing in heels could be _so exhausting_. How does your grandmother do it?”

“She’s a witch,” Rory said plainly and Jess snorted, mumbling, ‘ _You can say that again’._ She smacked him lightly and told him to behave.

“I’d go with but I don’t want to be a third wheel tonight,” Matt said. “I’m already feeling melancholic over my losses.”

“Aw,” Rory said a little sadly. “We wouldn’t let you be a third wheel!”

“Jess would,” Matt mumbled.

Jess smirked. “True.” His hand slid down to Rory’s butt and he gave her a firm squeeze. She jolted a bit at the pressure and glared at him.

“Stop that. We’re in front of our friends.”

 _“I really don’t think that’s a deterrent,”_ he whispered, pressing his other hand into skin of her back before slowly trailing it down under the edge of her dress’ low cut back. His fingers slipped under her thong and along the crevice of her backside.

“Ugh!” Matt groaned. “You guys really gotta keep your kinks confined to the bedroom!”

“We are in a bed room,” Jess said. “You guys can leave anytime.”

Rory wiggled out of Jess’ grasp, though she was a little unhappy to do so. She put her back to his chest so that her friends weren’t getting a full view of Jess’ crude actions. Lane looked slightly horrified, but Chris remained unfazed.

“Wow, you weren’t kidding about them being exhibitionists!” Her best friend said, looking up at Matt. She looked back at Rory with a look of slight disappointment and judgment. “This is _definitely_ worse than that time you had sex at Miss Patty’s.”

Jess laughed and wrapped his arms around Rory from behind to bring her in a little closer so that they were spooning. “Wait, you did _what?_ When the hell was this?”

“Lane!” Rory cried, blushing ferociously as she tried to squirm free of Jess’ hold. “We had a pact never to talk about that again!”

“Sorry but the pact was broken the moment your boyfriend just played with your thong in front of us all.”

Chris laughed. “And to think, that’s not even the worst thing I’ve seen them do. You know when I met this asshole for the first time, I definitely did not think I’d be here, witnessing him touch his girlfriend inappropriately as if there was no one around.”

“Besides,” Lane said, pointing an accusatory finger at Jess, “you promised that I’d never have to see you touch a woman inappropriately like this again after that stint with Dinah! You lied to me!”

“I can’t help it,” Jess said. “My girl’s really hot and I like to show my appreciation whenever, wherever.” He placed an open mouthed kissed on Rory’s neck and Lane practically screamed.

“Stop it! Stop it right now! Mama won’t even let me back in her house after this. She’ll know I’ve seen things! I already hear all the details, I don’t need to _see them._ ”

Rory ducked her head in embarrassment and scooted out of Jess’ arms for her friends benefit. “We’ll stop now. Right, Jess?”

“Fineee,” he said, rolling his eyes. “But when we go out I’m totally going to—”

“ _Okaaaay!_ And on that note,” Chris said, effectively cutting Jess off, “I’m taking Lane to up to bed now and away from you sexual deviants.” He put a hand on Lane’s shoulder, guiding her toward the door.

“Oh, thank god!”

“Yep, coming with!” Matt called after them just before he gave Jess and Rory one final look of disgust, but Rory could see a bit of envy there too and she had to hold back a giggle. “Goodnight you disgusting, lucky animals. Do yourselves a favour and don’t get arrested for public indecency.”

“We’ll definitely do our best,” Jess said.

“Also,” Matt said, crossing his arms over his chest just after he checked to make sure Lane and Chris were really gone, “you owe me for making me want to douse my eyeballs in gasoline. I want a Lane.” He was looking directly at Rory now, eyes narrowed. “You can’t just give Chris a friend and not give me one, too.”

Rory smiled sheepishly. “The only other friend I really have is Paris. There’s Lucy and Olivia, but I haven’t talked to them since graduation, honestly.”

“And you?” Matt asked Jess, and her boyfriend just shrugged.

“All the girls I know, you know.”

Matt grunted. “Fine! But I refuse to spend another year single and alone. I gave you a job, I made sure you had a roof over your head when you were first moved to Philly, stubborn and depressed. You’re gonna play wing man for me the next time we go out, you hear me?”

Jess laughed, but Matt just glared at him. “Okay, man! I hear you. I’ll play wing man.”

“Good.” Matt looked happier now. “Goodnight then. Happy fucking.”

When he was gone, Rory clasped her hand over her mouth and giggled. “I feel so bad for him, but he looks so funny when he’s mad.”

Jess snorted, moving to get up out of their bed. “C’mon, let’s get you fed.”

She turned on her side to face him, a playful smile on her lips. “Room service?”

“I thought you wanted to go out,” he said, laying back down and tracing patterns along the skin of her back.

“Well, that was before you started touching me,” she said, walking her index and middle finger up his chest and to his neck. “Besides tonight has been a roller coaster and you are the perfect person to wipe my mind clean.” She slid her hand into his hair and brought him in for a long, full kiss.

Jess moaned appreciatively into her mouth, and Rory pushed him down flat on the bed and straddled his hips, her long dress bunched up around her thighs. Jess’ hands found her skin and he stroked her with his thumbs, inching up a little higher. She melted a little at his touch, and moved to unzip her dress from the side, letting the straps fall from her shoulders. Jess helped to pull her arms out of it and pulled it up over her head.

“Just as beautiful as the first time,” he mumbled, skimming his thumb over her nipples until they puckered.

The night flew by quickly with the sounds of rustling sheets and quiet moans of pleasure. Rory felt herself fading into sleep on Jess’ chest after the first two rounds when he called for room service. He kept his voice low so as to not disturb her, and asked what time the kitchen closed. She supposed it was still open, even at almost one in the morning, as Jess asked for the food to be charged to his own credit card instead of the one on file. Rory fell asleep soon after, but awoke once room service came with their food.

She was groggy when she got up to eat, but her fish tacos were so flavourful that they pretty much woke her right up. Rory dipped it into her cilantro lime sauce and took a big, hearty bite. She polished off her fries after and tackled the strawberry cheese cake Jess ordered them for dessert. When they’d finished, she got up out of bed and made her way over to the dresser to find the pyjamas she’d unpacked earlier.

“What are you doing?” Jess asked.

“Getting ready for bed, silly.” She grabbed a small pair of silk shorts and slipped them on, searching for a tank top to wear with it. “If you think you’re going to be covered up while I’m not, you’ve got another thing coming.”

Jess whistled at her, nice and low. “You should just stay like that,” he suggested flirtatiously, getting up out of bed to kiss her. She pressed herself against him, chest to chest and toyed with the hair at the nape of his neck when his hands slipped down her back to grab at her cheeks. “Are these even shorts?” He teased, playing with the hem of them. “They barely even cover you.”

“They used to fit better before,” she said, feeling a little embarrassed. “But I gained weight so…”

He squeezed her again. “I’m not complaining.”

“Did you know my mom sang Sir Mix-A-Lot the last time she saw me? She’s just jealous because she doesn’t have an ass. When I was younger, I wore a skirt of hers and she got mad because she said my huge ass was going to stretch it out. Said the same thing with boobs, too, even though mine are _most definitely_ smaller than hers.”

Jess laughed and let his hands slide right back up to her waist. “Your ass _is_ very nice. It’s round and firm, a very good shape. When you turn to the side, you’ve got that very attractive curve going on. I am a fan.”

“You’re an ass man aren’t you?”

“What gave it away?” He asked playfully, nuzzling her cheek with his nose.

Rory rolled her eyes but leaned in to kiss him all the same. “Your butt is much nicer than mine, actually.”

“Huh. You’ve been checking me out?”

“Since we were sixteen.”

“Wow, Gilmore. Scandalous. If only poor old Dean had known.”

She smiled at him, suddenly feeling very happy.

“You good?” He asked her seriously. “I know tonight was a lot for you…”

“I’m _very_ good,” she promised with a nod and a flash of her teeth. “You always make everything better.”

“Not always,” Jess said, licking his top lip and glancing away. “I know for a fact I’ve made a lot of things worse for you in the past.”

She moved out of his embrace to drag him back to the bed. “No. Jess. the only thing that made things worse for us was the fact that we were constantly living in denial about our feelings. But now? Now we’re not doing that. We’re together, me and you, the way we were always meant to be. That’s why Logan got upset, anyway. I told him about us.”

“You did?”

“Yes,” Rory said with a deep breath. “I’m happy with you and I don’t want to hide that from anyone. If they can’t accept it then, tough. I’ve waited years to be with you and now I am, and if anyone thinks that I’m not going to enjoy every single second of every day I spend with you then they’re insane.”

Jess gave her a true, soft little smile and Rory felt her knees go weak. She sat down on the bed and grabbed his hand.

“You’re happy too, right?” She asked.

Jess laughed and cradled her cheek in one of his hands. “I’m the happiest I’ve ever been.”

There was a spark behind his eyes that Rory had never been before, and it hit her that it looked like he was on the verge of tears. She scooted in a little closer and wrapped her arms around his shoulders to hug him. He pulled her into his lap so they could be closer and he hugged her back so tight she thought they’d meld together, but she didn’t mind. She laid her head beneath his chin and closed her eyes, just happy that they were finally here together.


	10. Chapter 10

**Notes for the Chapter:**

> Ahhh, okay I wrote this all on my phone so hopefully it's okay.  
> My fingers are cramped now and i'm lowkey suffering, but thats fine.
> 
> I hope y'all like this chapter and the parallels between past and 2008! (: As always, let me know what you think in a comment below!!

**AGE TWENTY-ONE. NOVEMBER. HARTFORD**

Jesscalled her at seven in the morning on a Saturday just as her grandmother tried to get her up. Had it not been for seeing Jess' name on her phone, Rory would've shoved her face into her pillows and demanded for at least an hour more of sleep. But, the moment she saw that name in big block letters, Rory shot up out of bed and practically slammed her phone to her ear.

"Jess?" She asked, trying to keep her excitement at bay. He hadn't called her back at all since he'd gone out to Philly, requiring her to get all the latest news from Lane and Luke. Things seemed to be going well for him out there, so Rory did her best to make sure she wasn't acting bitter or angry. He needed to go and live life on his own terms, she understood that more than anyone.

"Hey," he said quietly and Rory's pulse spiked at the sound of his voice.

"Hi," she laid her head back against her pillows. "How are you?"

"Okay. I got your message, I'm sorry I didn't call back sooner but I've been busy. How are you doing?"

Every word threatened to bring tears to her eyes, but she didn't want him to hear her crying. He never did well whenever she cried. She took a deep breath through her nose and exhaled quietly through her mouth.

"Good... I'm good. A little bored, really... Been helping my Grandma with the DAR and you know... community service."

"So, you're still at the grandparents then."

Rory swallowed thickly, trying to ignore the way he sounded disappointed. "Well, yeah. My mom and I are still fighting and..." she shrugged. "You know how she is..."

"Thought you guys were doing better after your birthday."

"Not really. We're still kind of estranged."

Jess sighed and Rory stared up at the ceiling. No matter his disappointment she was just happy that he'd bothered to call her at all. She missed the sound of his voice and the way he talked so simple and to the point.

"I'm sorry that things aren't fixed."

"Why are you apologizing, Jess? You have nothing to apologize for."

"I wish I were there to help is all."

"No," Rory said firmly. "You're doing big things for yourself out in Philly. You don't need to come home and be my prince in shining armour."

"Right," he said it a little awkwardly and Rory felt her stomach drop. She knew what was coming next. "How's Logan?"

She swallowed against the hard lump in her throat. "We're on a little break right now."

"Really?" He asked and Rory could tell he was trying not to sound too interested. "How come?"

She shrugged a little again. "We got into a fight."

"About what?"

"You," she admitted, biting her lip. "He doesn't like that we're friends... and we got into an argument and now we're just taking time to clear our heads. I'm sure everything will be back to normal by the New Year."

"How long have you not been talking?"

"I don't know. Maybe a month or two."

"And you're sure he knows it's a _break_ and not a _break up_?"

"It was one fight. People don't just assume they're broken up over one fight, Jess." Logan was smart enough to know that, she was sure.

"Okay."

"Anyways," she wiggled down into her blankets with a smile, banishingaway all thoughts of Logan. "How are you? How's Philly? Tell me everything."

"There's really not much to tell. I met up with Ajmal's contact, he introduced me to some cool guys who run a publishing company called Truncheon down on Locust street. There's four of us, it's smelly, but nice I guess."

"It sounds so cool! I can't wait to come and visit."

"You should focus on your own stuff first," he argued and Rory pouted. "Like fixing things with your mom."

"She's the problem! Not me!"

"Okay, well, what about Yale, are you going back anytime soon?"

"I've ... been thinking about it, yeah. Maybe next semester."

"Does your mom know that?"

"No."

"You should tell her. It'd probably fix everything."

"No, I shouldn't tell her. She's rude and she doesn't understand me."

"She understands you better than anyone."

"Not better than you."

"Rory," Jess sighed.

She pushed herself up to sit in bed and dragged her knees up to her chest. "I know that I literally just said you shouldn't come home because you're doing big things in Philly, but... maybe a visit wouldn't hurt?"

"Rory—“

"Please, Jess?" She begged, her voice thick with the tears she'd forced back earlier. "I just really, really need you right now." A few tears started to leak and her throat got scratchy. "Please come home." She didn't mean to start bawling, but the sobs came faster than she could choke them down. "Please, please, please come home. Even if it's just for a minute. I just want to see your face."

There was silence for a few beats, nothing but the sound of Rory's sniffles and quieting sobs.

Finally, Jess said, "Okay. I'll try."

 

**AGE TWENTY-THREE. AUGUST. HARTFORD**

Jess didn't know how he felt about being back in Stars Hollow. Obviously, he'd been here just a few months ago to talk to Luke and Lorelai, but now he was here with Rory as a couple.

They hadn't necessarily planned on visiting for long after the Gala, but Lorelai had called Rory and begged her to swing by. They had to drop Lane back home anyways, so it wasn't like it was out of the way. The moment they'd entered the crapshack, Luke let them know they were due at the Gilmores for dinner.

Jess tried to fight it, saying they had to get back because Matt and Chris were their ride, but his friends turned their back on him quickly. They said that Jess should take a few more days off to catch up with his family, and Lorelai had even chimed in that she'd drive the two of them back home. Rory had, of course, gotten so caught up in her excitement that she wound up agreeing for the both of him, and now here he was, at the Gilmore manor, sitting at the dinner table like he was eighteen.

He was jealous that Luke had somehow managed to get out of it.

"So, Rory, Jess. How is Philadelphia treating you?" Emily asked a little coldly. She'd made it rather clear that she didn't like Rory living so far away Connecticut, and she'd blamed Jess for being such a powerful (synonym for negative, he was sure) influence.

"Good, Grandma. Jess is working on his new book, and I've gotten quite a bit more bylines at work this year."

"Oh, we know! Your grandfather and I read all your articles. Don't we Richard?"

"Oh yes," Richard said, looking proud as could be. That made Jess smile a little, he liked knowing Rory had a strong support system. "You're the sharpest writer of the bunch! They should be promoting you in no time."

Rory bowed her head, blushing a little. "Oh, I don't know about that..."

"Well, you certainly should!" Richard boomed. "You're a Gilmore, after all! And even better yet, you were the chief-in-editor at the Yale Daily News. That is no small feat, m'dear!"

"Thanks, Grandpa."

"Mhm," Richard nodded, seeming satisfied now.

"So," Emily spoke up again, her dark eyes zoned in on Jess, "a new book?"

Jess nodded. "Yeah. It's in the early stages." Emily narrowed her eyes, so he continued. "It's about love and life. The people we meet... how they impact you. I don't know, it's kind of jumbled up right now."

"Wow," Lorelai said from across the table. "How romantic."

Jess glared at her.

"Why, yes," Richard agreed. "That is quite the romantic topic. I never took you to be the type. Is it inspired by anyone in particular if you don't mind me asking?"

Lorelai grinned, an evil glint in her eye. "I'd like to know too."

He looked at Rory for confirmation and she looked back at him, shrugging with a smile. The book was new. Really new. Like fresh fallen snow new. He'd come up with it after sex in the hotel on their last night in New York. It came to him easily so he'd started writing it down in one of the free hotel notebooks. Rory had watched him over his shoulder and somehow it'd been inspiring to let go of his thoughts and just write lucidly. She'd wrapped herself around him, placing small kisses to his neck and he'd been overcome by the relief and the joy he felt at just being with her that the words just spilled out of him and onto the page.

"It's inspired by Rory," he admitted, “and our relationship."

Emily put down her fork and stared at them, then at Lorelai and finally at Richard. Then she went back to Lorelai. "You said the two of them weren't together."

"Hey, they weren't when you asked!"

Emily looked back at Rory and Jess. "When did this happen?" She demanded, voice sharp.

"Um..." Rory reached for his hand under the table and Jess gave her a firm squeeze. "About two months ago? June."

Emily studied her, as if expecting to catch her in a lie. "Well, good then," she said stiffly, picking her fork back up.

Rory looked between her grandparents. "Good?"

Richard shrugged. "Your grandmother and I had our suspicions about your relationship. We were simply waiting for confirmation."

"And... you're fine with it?" She asked, looking back at her grandmother specifically, a little confused.

"You've never cared about what I've had to say."

"Nor I," Richard said easily.

"That's not true," Rory argued. "I sought out your approval for a long time. The fact that you loved Logan was a very important aspect to making my relationship with him work. I want you to like who I'm with."

Jess looked down at his lap, his hands were starting to get a little clammy. He'd been afraid of this conversation. He knew Rory had issues with what other people thought of her, which was why he hadn't wanted to cross the line in the first place. He hoped that Emily and Richard didn't ruin their happiness in one fucking night.

"I like Jess just fine," Richard said with a shrug. "He's exceptionally bright. Good taste in literature and music. He knows how to keep you happy, always has. I've considered him family since you made it very clear he wouldn't even leaving our lives anytime soon, _ever_ , as your seventeen-year-old self so eloquently put it. Still quite disappointing that he never went to college with that brain of his but he's made something of himself none the less. I respect that in a man."

Rory sat up a little taller and clutched Jess' fingers like a vice as she beamed. "Aww, Grandpa..."

Emily sighed. “Well, I, for one saw this coming from years ago. I surely believed that after you and that Dean boy broke up that Jess was next in line but you skipped straight to Logan. You two were a darling couple, Rory, and I will be forever disappointed that the two of you couldn't work things out but as your mother once said to me—your life is yours and if Logan made you feel as if it wasn't then I certainly can't continue to cry over the loss of that relationship now can I?"

"No, you can't," Rory said confidently.

"It was only a matter of time before the two of you got together anyways." Emily rolled her eyes as she cut up her meat, took a bite, chewed and swallowed. "I just sincerely hope you can make it stick. When your grandfather and I were young being close so twenty-five and unmarried was a disgrace."

"We aren't in your time anymore, Mom."

Emily fixed Lorelai with an icy glare."Rory was proposed to once already. People will talk if she's not married soon."

"Who?" Lorelai asked. "Whose gonna talk, Mom? The DAR ladies? Shira Huntzberger? Other rich cronies? They just figured this thing out. Just give them some time to breathe before you shove the idea of marriage and children down their throats. Yeesh."

Rory gave Jess a watery smile before letting go of his hand, mumbling, "Oy with the poodles already."

Jess tried to smile back at her, but he suddenly found himself feeling very nauseous.

 

**AGE TWENTY-ONE. DECEMBER—GILMORE HOLIDAY PARTY. HARTFORD**

Rory actually liked her grandparents annual holiday party. She'd liked it as a child, even though her mother had done everything in her power to make Rory hate it, and she still liked it now at twenty-one. The food was great, the music was definitely nice, and Rory actually enjoyed being in the company of her grandmothers friends—she liked them all more than Grandma did, anyway.

She'd always been a planner, too. Lists, organization, multi-colour pens--the works! So, she was more than happy to help Grandma plan this years event, she'd even successfully dodged all questions about Logan in the process. It was easy enough to say he couldn't attend, after all the Huntzbergers had their own family traditions and her grandparents couldn't have expected him to just give them up for the Gilmores.

Grandma was obviously disappointed that Logan wouldn't be joining them this evening, but Rory didn't mind at all. Sure, she missed him, a lot, but he'd asked something impossible of her. He'd asked her to give Jess up, and that just wasn't going to fly. She was steadfast in her defence of Jess and she was determined to remain so.

"Ah, Rory! Everything looks wonderful," Grandma said looking around the living room with a look of pride. "You were born for this!"

Rory smiled, feeling as if that wasn't exactly true, but she also liked the compliment. "Thank you, Grandma." She knew better than to say it was easy, even if it had been, because she didn't want to insult her grandmothers craft.

"The guests should be arriving any minute. Go on up stairs and get dressed before they arrive, we wouldn't want to be caught looking a mess. Your mother will do enough damage for us as it is."

Grandma had been making zings like that toward her mother for months. She probably thought that now that Lorelai and Rory were out on the outs that Rory would enjoy hearing her mother insulted, but she didn't actually like it at all. She opened her mother to argue, but Grandma just steered her up stairs and shooed her away, telling her not to come back down until she looked absolutely perfect.

Rory sighed and trudged back up to her "room", and found a dress that her grandmother had picked out for the occasion. It was a beautiful cranberry red, very tastefully cut. Definitely wasn't ugly, Rory decided as she laid it down on her bed next to the matching shoes and gold jewelry.

 

It took her about an hour to get ready in the end and when she made her way back downstairs, some guests had already arrived--including her mother, Luke, and Jess. Rory stopped when she caught sight of him, holding onto the wall in her shock. He looked beautiful in a blazer and dark black button up with matching pants. His hair was cut short again, slicked back in a way that reminded her of high school but it was a little cleaner.

He smirked at her, nodding once. "Hey," he said effortlessly, as if they hadn't just spent almost three months apart.

Rory broke into a wide grin that hurt her cheeks as she ran to him, garnering the attention of guests when she squealed and wrapped her arms around him as tight as she could. His arms lung limp at his sides for a beat before he embraced her back, burying his face into her hair.

"You came!" She said, finally letting him go. "Back to Connecticut, I mean."

He smirked at her. "I did. Only for a little visit. I have to get back to Philly before the New Year."

Rory didn't let that news get her down, she was just happy that he was here at all. He looked a little scruffier than she was used to. There was some stubble growing on his jaw and he almost looked rugged. She wanted to reach out and touch his chin, stroke the skin there but she kept her hands to herself.

Beside Jess, her mother cleared her throat. "Yes, hello darling daughter of mine. It is I, your mother, who carried you for nine months and suffered through childbirth to bring you into this world only for you to run to pretty boy over here and ignore my entire existence. I see how it is. A mothers love is worth nothing anymore."

Luke, Rory, and Jess all rolled their eyes.

"Hi, Mom," Rory said, trying her best not to sound annoyed. "Merry Christmas."

"Can I at least get a hug from my only child or am I such a demon not even that can be done?"

Rory shuffled forward a bit, extending her arms out so she could hug her. They stood there for a moment, awkwardly embracing until Rory broke it to look down at her shoes.

She heard her mother sigh in disappointment.

Rory looked back up but she focused on Luke instead and smiled at him, a real genuine one--after all, she wasn't mad at him. "Merry Christmas, Luke!" She said brightly, ignoring the blatant look of shock and hurt on her mothers face. "How's Stars Hollow and April and the diner?"

"Oh!" Luke looked a little taken aback at the question. "Good, good. Everything's good... April is good. Stars Hollow is cooky, and the diners the same..." he nodded awkwardly, shoving his hands into his slack pockets and pursing his lips with a smile.

"That's good," Rory said, turning her attention back to Jess. "Would you like a drink?"

"I know I would," Mom grumbled, grabbing Luke's wrist and dragging him off into the living room.

Jess looked at Rory, eyebrows raised. "A little harsh, no?"

"What? I said Merry Christmas and gave her a hug! What more does she want?"

Jess shrugged.

"Do you want a drink?" She asked, huffing a little bit. "Grandma hired a bartender. He does really fancy egg nog. I had to sit through three hours worth of bartender tests. I was very drunk in the end."

Jess chuckled. "I'll bet."

"It was fun though!"

"Yeah?"

She grinned at him. "Oh yeah." There was no way she was going to tell him that she'd spent hours in bed getting off that night, but she let a little saucy tone slip into her words to convey it subtly.

"So, what made this guy win out over the others? His egg nog that good?"

"It's the best. So boozy and thick, too! You'll love it."

"I come back after two months and the first thing you wanna do is get me drunk?" He said lightly, teasing her in that way that made her blush.

"Well, Santa Claus isn't very pleased with me this year."

Jess laughed and it sounded like music to her ears. She leaned in and kissed him on the cheek, but it didn't feel like enough so she kissed him on the other one, too.

"Are we French now?"

She blushed. "Shut up! Lots of cultures kiss each other on the cheek in greeting, including the Italians. I'm just taking a page out of your people's book."

"Is that right?"

"Yep," she nodded and grabbed his hand to drag him off to the bar. "That's right."

When they both had a fancy egg nog in their hand, they snuck up to her room to escape the party. Jess didn't do well with big parties surrounded by people he had little to nothing in common with, and even though his life was better now, Rory hated seeing the way in which people reacted when Jess said he wasn't in college. It was just easier for the two of them to leave and talk in private.

Besides, Rory had long noticed that Jess was carrying around a gift bag with her name written on it and she really wanted to see what was inside. She'd tried to sneak a peek while they were getting a drink but he'd glared at her and held it away from prying eyes, promising to give it to her when they were alone. She didn't comment on how dirty that sounded, reprimanding herself for even going there. 

Rory sat cross-legged on her bed, making grabby hands for her present. "Gift me!"

Jess rolled his eyes. "You're impatient, you know that?"

Rory just smiled and nodded, happy when he finally handed it over. She threw the red tissue paper onto the floor and looked inside to find a small book and a card.

"Read the card after Christmas or something, okay? I'd rather not be here for it," Jess said, and she looked up to find his cheeks red.

"You're blushing!"

"No, I'm not."

"You are!"

"Would you just look at the present!"

Rory grinned, not taking her eyes off of him as she reached into the bag and pulled out the book and the card. She placed the card down onto the bed and took in the dark cover with a tree.

"The Subsect," she read aloud, looking down at the bottom for the authors name. She blinked at what she saw, uncertain if she was actually reading this right. "By Jess Mariano... you wrote a book?"

She looked up at him for the answer only to find him smiling a little shyly.

"Merry Christmas?"

"You wrote a _book?!_ " She asked again, getting up off her bed to pace around with it in her hand. "You wrote a book!"

"Short novel," Jess corrected, but she gave him a withering stare just before flipping through the pages.

"When were you going to do tell me you wrote a book?!"

"Today."

_"Jess!"_

_"Rory,"_ he mimicked her tone, but it wasn't quite as loud.

She sat back down and held it to her chest, feeling a little faint. "You wrote a book..."

"That's the first copy. Well, one of five copies, really. We're going to do a whole run sometime next year with an open house... that's just the trial print."

"I got a first edition?" She asked, feeling like she was going to start weeping. Why did he always make her cry?! What kind of magic was he loaded with? "Jess... this is so incredible."

"It's not that great."

"No, it is! It's _SO_ great! You are so talented and so smart and I knew, I just knew that you could do something like this. You have a great brain, and I knew if you could just sit down and stop shaking it around that you could do something like this. I knew it, I knew it."

"I know you did." He was looking at her so softly that her heart hopped up into her throat. She swallowed to put it back in place, put the book onto her comforter and stood up to give him a hug. It felt weak, she wanted to do much more than wrap her arms around him but she knew she couldn't.

"I'm so proud of you," she said, burying her face into his chest. "I'm so, so, so proud of you..."

"I just wanted you to know that I couldn't have done it without you."

She shook her head against him. "That's not true. You would've done it either way."

"I did it faster with you. You make me want to be better--to do better for myself."

Rory pulled back to give him a fresh smile. "I'm glad, Jess. I'm so happy for you!"

He smiled back at her just before she started pacing and skimming the book again. "This makes my present look really lame."

"I doubt it. I'll love anything you get me."

She threw him a disbelieving look. "Even that giant prescription pill coffee mug?"

"You know you didn't buy that for me, you bought it for yourself."

"True," she said, grinning. "Makes me feel special that I have my very own cup in your house."

"You're a menace, Gilmore."

She hopped back into her bed and got comfy amongst the pillows. "Since I can't read the card, can I at least read the book in your presence?"

Jess winced. "I'd rather you didn't."

"Oh come on! You have to be proud of this Jess, this is a huge accomplishment!"

Jess shrugged. "I think the guys were high when I met them and they said they wanted to publish it."

Rory stared at him. "No they were not."

"Hey, you don't know. You weren't there."

"They want to publish you because your work is good!"

"You haven't even read it yet."

"So?"

Jess laughed a little. "So read it before you get too jazzed about it, okay?"

"Are you writing a sequel? You should write a sequel."

" _Rory_."

"Okay, okay," she said just as her phone started to ring on her desk. She looked at the time, knowing who it was, and didn't move.

"Aren't you going to get that?"

"No."

“Why not?"

Rory crossed her arms over her chest and glowered at her phone. "Because it's Logan and I don't want to talk to him. He calls me around this time every two weeks or so."

Jess sucked his lower lip into his mouth and nodded, nice and slow. "And you think not answering is a good idea?"

"I don't want to talk to him, so yes."

"Mm. Okay."

Rory sighed, feeling grateful when her phone stopped its vibration. She laid back, legs still crossed, as she looked up at the ceiling. "He can't decide who my friends are. I'll talk to him when I go back next semester."

"What's going on with you, Rory?" Jess asked after a moment of silence. "Working at the DAR? Not talking to Logan for months on end? Treating your mom like shit? That's not you."

"Well, maybe it is now," Rory defended, but it was a weak comeback and she knew it was weak.

Her resolve had been cracking for a while now. Her anger at her mother was real. She was still angry that her mom kicked her out for wanting to take time off of school. She was angry that her mom hadn't been supportive of her in the slightest during the hardest time of her life. She was angry that her grandparents treated her like a re-do of their botched hand at raising her mother. She was angry that she let Mitchum Huntzberger get to her as badly as he did, that she dropped of Yale, and had gotten so sloppy in handling her feelings for Jess that it'd almost ruined their friendship and her current relationship. All in all, Rory was angry about a lot of things.

"And besides," Rory started up again, trying her best to put up a fight, "you _left_! You just left me, _again._ "

Jess rolled his eyes. "Don't try and shift the blame right now, okay? You knew I was leaving, I told you I was. You thanked me for telling you that I was! I tried to get you to go back to Yale for months before I left, Rory. You didn't want to listen."

"You didn't take my calls for a whole month after you were gone," she said quietly, all the fight knocked out of her already. She clasped her hands in her lap and stared down at her knuckles, unwilling to face him. "I told myself it wasn't personal and that it didn't hurt, but it did. It hurt, Jess."

"Rory..." he sighed. "I'm sorry. I wasn't in the right headspace, and I just needed to figure stuff out on my own for once."

She shrugged. "Maybe that's what I need too," Rory said, looking back up at him. "To figure this out by myself."

"Yeah, but ... dropping out of Yale? Rory, that's not you."

"How would you know?" It was childish and petty, she knew, but she said it anyway.

"Because I know you. I know you better than anyone, even your mom. Your words by the way."

She smiled a bit, unable to fight against the upturn of her lips.

Jess knelt in front of her, his hands on her thighs in a way that made them burn. She always felt this way when he got a little too close, and if she thought about it for too long, the desire to reach for that locked box underneath her bed overpowered her.

"You said you wanted to go back next semester, right?"

She nodded, not trusting herself to speak.

"Okay," he said, his voice so soft that she barely heard it. "I really think your mom would like to know. It'll be the first step to mending fences. I'm not saying she was right in her reaction, I'm just saying that she's your mom and you love her and being away from her is making you miserable. So... fix it."

"I can't," Rory said miserably. "I've been so awful to her that I don't know how to act normal anymore."

"You'll figure it out," he promised. "You just have to want to."

 

**AGE TWENTY-THREE. AUGUST. STARS HOLLOW**

The rest of the time spent back in Stars Hollow was nice and quiet--for the most part. They hadn't bothered announcing their relationship to the town in a PSA, but everyone was talking when they held hands and kissed in public. They spent their nights at the apartment above the diner, and Rory had come down one morning in nothing but his old distiller shirt and boxer briefs. Lorelai told them the story of how she'd done something very similar.

Miss Patty and Babette watched them like a hawk, whispering to each other and giggling. Jess did his best to ignore them, especially whenever they tried asked Rory what his dick looked like and how good he was in bed.

Jess spent most of his time upstairs trying to write, but the words weren't coming to him quite as easily now. It was their last official night in town, Lorelai would be driving them back to Philly tomorrow, and Jess couldn't have been happier to go back. There was something about this place that kind of fucked with his head, but on top of that he couldn't get Emily Gilmore's words out of his head.

He'd never considered himself the married with children type. When he told Avery that he didn't believe in The One and all that bullshit, he hadn't been lying. Yes, he loved Rory, and he was gearing up to tell her that soon, but suddenly he was starting to worry about what she expected from him. She'd turned down Logan's proposal, citing her future and career as the reasons why and he knew that Rory was serious about that, but they were getting older now. They'd both be twenty-four by the time the year was over, and they really hadn't been dating all that long officially, but what if Rory didn't see it that way?

Thinking about it was giving him anxiety. He wasn't ready to propose to Rory Gilmore. Maybe one day he would be, but definitely not any time soon. He had a hard time thinking that was even close to what she wanted anyway, and bringing it up would probably scare her off. Jess groaned and laid his head down against the kitchen table just as Rory came out from the bathroom.

"What's wrong?" She asked, running her fingers through his hair.

"I don't know," he mumbled.

"Do you have writers block?"

He lifted his head to rest his chin in his palm. "Possibly. I've been thinking about it too much, it's tripping me up."

"About the book? Or us?"

"Both, I guess."

Rory hummed and plopped down in his lap. "You've been kind of a sad puppy since we finished dinner at Grandmas."

"No, I haven't," he tried to deny.

Rory stroked his cheek with her knuckles. "Jess, I know you exceptionally well. I can tell when you're happy, sad, angry, bitter... I know every single side of you. You can't hide from me. Just tell me what's wrong. Is it about what my grandma said?"

"Maybe."

Rory sighed. "Thought so. Her feelings aren't mine. I'm happy with where we are right now."

"Yeah?"

She laughed. "It's been two months, you think I want to get married all of a sudden. Check back in," she hummed in thought, "two or three years. Twenty-six is a good age, and it's a year older than Grandma would want for me."

He wrapped his arms around her waist, laughing against her neck. "You're a cruel woman."

"Hey, she doesn't get to dictate when I get married. _If_ I get married."

"If?" Jess repeated, intrigued.

"Yeah," Rory said a little insecurely. "I don't know? I just... I always saw myself as the marriage type. I'd get married and have kids and a nice home and maybe a dog and a cat, too. But then... I don't know, it was presented to me on a silver platter and I didn't want it."

Jess nodded against her shoulder.

"It made me wonder if I want that at all, you know?"

"I do."

"So, no pressure from me, I promise. Just ignore my grandmother, her thoughts and opinions are not reflective of mine."

Jess placed little kisses on back, moving her hair to the other side. "I'll definitely keep that in mind."

"And the next time she freaks you out, just tell me, okay? We can combat her together."

"Battle couple?"

Rory grinned with a nod. "Matching swords and all."

 

**AGE TWENTY-ONE. DECEMBER--JESS' BIRTHDAY. STARS HOLLOW**

Since her grandparents holiday party, Rory couldn't stop thinking about all that Jess had achieved in the two months he'd been gone and everything he'd said in her bedroom. She knew that The Subsect had to have been something he'd been working on for quite some time, but to be on his way as an officially published author before he was even twenty-one was straight up remarkable.

In a way she was as jealous as she was proud. Jess was her best friend and she'd been defending him to everyone since they were practically kids. She knew he was destined for greatness, that he was talented and smart, but she'd never counted on falling behind.

It was she who had gotten the fancy high school education, and it was she who had been enrolled in Yale. She had all these dreams about being the next Christiane Amanpour, travelling the world, maybe working for CNN. Failure had never been an option in her mind, and if these past few months had taught her anything it was that failure was still not an option.

Jess Mariano had nothing but a high school degree, and yet he'd found a way into his dream job (the dream job he hadn't even known he wanted) and if he could do it, she could too. So what if Mitchum Huntzberger was an asshole? Rory was a Gilmore and Gilmores were bulldogs, they didn't give up.

And that's why after her grandparents headed off for their vacation in Martha's Vineyard, Rory wrote them a goodbye note, left it in her grandfathers study, packed up her car and drove back to Stars Hollow on Christmas Eve.

 

**AGE TWENTY-THREE. AUGUST. PHILADELPHIA**

The ride up to Philly went by quickly for Jess, considering he slept almost the whole way. The talk he'd had with Rory on their final night in town had done wonderful things for his creativity and his sex drive, so he'd hardly gotten any sleep at all.

Rory and Lorelai were, of course, hopped up on coffee and singing away to songs on the radio and playing silly road games, but Jess was far too tired to care. By the time Rory shook him awake they were in the underground garage of their apartment building and Lorelai was off waiting by the elevators.

"I just realized something," Rory said, sounding nervous. "Mom's gonna know we've been sleeping in the same bed."

"So?" Jess said, stretching before slipping out of the car with his bag and shutting the door. "We're dating."

"Yeah but.... I kind of told her that I had my own room at your place and that one of the boys had moved out to accommodate me... I made it a whole big elaborate lie because I didn't want her judging me for sharing a bed with you when we weren't together. I knew she'd probably think I was dumb for it and be disappointed, so I just... lied. I thought that by now I'd have my own place but obviously that didn't happen and now she's here and I'm freaking out!"

Jess didn't know what to say to all of that. He took all the information in, processed it, and just stared at her in disbelief.

"Why wouldn't you just tell her the truth?"

"I just told you why! Besides, Luke would've skinned you alive! I was protecting you."

"You're the one who jumped me in the middle of the nigh!”

"That was one time! And you were into it!”

"Of course I was into it, but you made the first move. You preyed on me. You should be the one skinned alive."

"Fine, when Luke inevitably finds out about this, I'll let him know that it was me who tried to have sex with you and not the other way around. I'll even tell him about how you rejected me and slept on the floor."

"I appreciate that," Jess said, smirking.

Rory rolled her eyes at him just as Lorelai poked her head out from the elevator room.

"What is taking you guys so long?!" She demanded. "Hurry up! Mommy has to tinkle!"

Jess gestured Rory forward. "After you."

They rode up to their floor in mostly silence. Lorelai talked the whole way, but Jess didn't engage, while Rory gave her mother half-hearted answers. They stepped out of the elevator and almost made it to their door when Rory decided to spill the beans.

"Mom, before we go in there I have to come clean.... Matt and Chris still live there, it's the four of us in a two bedroom place... and ..." she took a deep breath, closed her eyes and said the next part really fast, "Jess and have been bed buddies since November."

Lorelai stopped dead in the hallway, her blue eyes cold and narrowed in a way that reminded Jess of the Gilmore matriarch. It was freaky how they could all look possessed by the devil himself like that.

"You've been what?" She asked coldly, and Jess could see how hard Rory gulped. "Rory, you lied to me! We don't lie to each other!"

"I-I know!" Rory stuttered, fiddling with her suitcase handle nervously. "It's just that I didn't want you to judge me or get angry with me."

"Rory, you're twenty-three! You can do whatever you want no matter how I feel about it!"

"I know but that's never stopped you from judging me before!" Rory argued back. "And I don't like it when you do that, it makes me feel stupid. So, yes, I lied to you but it was for my own protection, Jess' protection, and the overall greater good!"

Their voices were starting to carry, so Jess quickly made his way to their apartment door to let them in. Matt and Chris must've been out or still sleeping as the door was locked. Jess shoved his key in quickly and stepped into the dark apartment, noticing the couch was neatly folded meaning Matt wasn't home.

Rory and Lorelai stepped inside, still bickering.

"I can't believe you think I'm that judgmental!"

"Well, you are!"

"And you!" Lorelai whirled to face Jess. "You've been taking advantage of this situation the whole time, haven't you? I bet you just _loooved_ that Mr. Greene was an asshole landlord so you could prey on Rory. _'Oh, don't worry Rory you can live with me. Sleep in my bed. Maybe even fuck me, too'_ , right?"

 _And it begins,_ he thought.

"Don't attack him! It wasn't like that!"

"Oh really? It wasn't? So, you two really waited until you were dating to have sex then?" She scoffed. "Give me a break, Rory. I was young too, once!"

"That's exactly what happened!" Rory said, looking to Jess for backup. "Jess was the perfect gentleman. He's a real life prince, actually! He never, not once, touched me inappropriately, even though I would've killed for him to."

"Ugh!" Lorelai sneered in disgust. "There are somethings a mother does not need to hear, including how badly her daughter wanted to fuck her step-cousin!"

"I hate it when you get like this!l Rory shouted, and Jess moved to the back of the apartment to check if Chris was home--he wasn't. "This is exactly why I didn't want to tell you!"

She stormed off to their room and slammed the door just as Lorelai called after her with, " _YEAH, WELL, MAYBE IF YOU HADN'T LIED TO ME THIS WOULDN'T BE HAPPENING!"_

Jess rubbed at his eyes before pinching the bridge of his nose with a hard breath. Lorelai collapsed onto the couch and placed her head in her hands and Jess honestly felt a little bad for her.

"I'm... just going to check on her," he announced to the stifling silence and made his way to the bedroom. He could hear Rory crying through the door and he knocked softly to let her know he was out there. "Can I come in?"

"Yeah," Rory said through her tears, her voice still shrilly a bit.

He entered slowly and found her curled up in bed on top of the covers, face red and covered in tears. Jess sat next to her and stroked the top of her head. "She'll get over it."

"No, she won't. Nobody holds a grudge like Lorelai Gilmore."

"Your mom could never hold a grudge against you."

Rory sniffed and wiped at her eyes. "You say that now, but she'll constantly bring up how I lied to her this one time."

"Rory... c'mon, you and your mom have fought before. Hell, I'm pretty sure you've fought over me before. Is this really anything new?"

"No, but I want her to support us. For real."

"She does. She's just mad because you lied."

"But I had to lie!"

Jess nudged her over a little so he could lay beside her, face forward. "It hurts me that you think you had to lie."

"She's never liked you. Half the reason I never told you how I felt is because she never liked you. And then she didn't like Logan either, and that sort of helped me get over the stigma of needing her approval for everything but ... I knew if I told her the truth she'd pressure me to move out and living here was the only way I could be so close to you..."

He kissed her forehead. "I felt the same way."

"But if she knew that she'd tell me I was being stupid, especially when Avery came back into your life, so I just kept the lie going."

"I get it."

"But she doesn't."

"You just have to explain it, calmly. I'll mediate."

Rory sniffed again, hiccuping a little as he rubbed her back. "Everyday you shock me with how mature you've become."

"I try."

She finally smiled, and he smiled back. "You'll really mediate? Because out there you didn't do anything."

He laughed a bit, which made her giggle as well. "I was in shock. I've never seen a Gilmore Girls fight up close."

"It can get pretty ugly."

"So I see."

She snuggled a little closer. "Thanks, Jess."

"For what?"

"For being there--always. You really kept your promise. You've never let anything get between us."

He kissed her once he realized what she was talking about, taking slow sips and drinking her in. When he broke away, he smiled, teeth and all. "You remember that?"

Rory nodded. "I still have that card. Sometimes I read it when we're fighting or I'm feeling sad..."

"Huh."

"You really thought I'd throw out the first and only time you've told me you love me?"

"Well, when you put it that way," he teased, and he wondered if this could be the moment.

Rory was staring at him with shining eyes, still slightly wet from crying, but she didn't look upset anymore. She looked happy, serene-like almost. Ethereal, his mind thought, and he knew this was definitely the moment.

Jess threaded their fingers together and he brought her hand up to his mouth, kissing each knuckle.

"I love you," he said.

She stared at him, waterline overflowing again, and when she blinked the tears fell but there were no sobs. He leaned in to kiss them away and Rory laughed at the sensation before she took his face into her hands and kissed him hard.

 

**AGE TWENTY-ONE. DECEMBER--NEW YEARS EVE. STARS HOLLOW.**

_Rory,_

_I know these past few months have been hard for you, but I just wanted you to know I'm here. It might not have seemed that way since I left for Philadelphia, but there isn't a single day I don't think of you._

_I have your one and only message saved to my phone so I can listen to it over and over again. I just wanted you to know that I love you, too. Those words have never been easy for me to say, but writing them down is a little easier._

_I want you to know what no matter what does or doesn't happen between us, you're the most important person in my life. Whenever you need me, I'll be there, I promise. And no matter how many arguments we have whether it's over books, or our significant others, Yale, whatever it may be... there's nothing in this world big enough to come between us. I sincerely hope you feel the same._

_Merry Christmas,_

_Jess._

Rory reread the card with a smile, tracing his beautiful script with her finger before she closed it and held it tight to her chest. She could hear her mother and Luke talking in the living room, watching some show or movie, and the house smelt like delicious coffee and pop tarts, and Paul Anka was laying at the foot of her bed.

Everything felt exactly as it should.


	11. Chapter 11

**Notes for the Chapter:**

> Hello all!!
> 
> Sorry for the late update, but I've been kind of lazy recently. This chapter doesn't have much going on for present day, other than Lorelai and Rory making up and some Literati smut. The final scene is just a small little filler bonus thing, but I hope it amuses you as much as it amuses me. The past is a little more plot heavy and I'm sorry about Dean 2.0 but it had to be done!! This is officially the last of Dean though and then next chapter we get into the Truncheon Open House! (:
> 
> As always don't forget to comment and tell me all your thoughts.!

**AGE TWENTY-ONE. JANUARY. STARS HOLLOW**

YOU HAVE FIVE NEW VOICE MESSAGES.

TO PLAY YOUR MESSAGES, PRESS ONE: **1**

 

> _“Ace, I’ve called you at least a dozen times since Thanksgiving. Would you please just pick up the phone? I miss you.”_

 

WOULD YOU LIKE TO SAVE THIS VOICE MESSAGE?

TO SAVE PRESS POUND, TO DELETE PRESS SEVEN: **7**

 

NEXT MESSAGE:

 

> _“Rory, I get that you’re mad at me. I shouldn’t have demanded that you give up your friendship with Jess, okay? I get it. But, I miss you and I want to see you. Please just talk to me, let me know we’re okay? … Okay, I hope to hear from you soon. Bye, Ace.”_

 

TO SAVE PRESS POUND, TO DELETE PRESS SEVEN: **7**

 

NEXT MESSAGE:

 

> _“It’s almost Christmas and I miss you, Ace. I bought you such a pretty gift, you’re going to love it. I thought about swinging by your grandparents house but I know you wouldn’t want to see me, so I didn’t bother. Just… call me back soon, okay?”_

 

TO SAVE PRESS POUND, TO DELETE PRESS SEVEN: **7**

 

NEXT MESSAGE:

 

> _“Rory, this is the last phone call I’m going to make. It’s officially winter break and I haven’t heard from you since the beginning of November… I just want to talk to you, okay? I don’t care if you’re friends with Jess or whatever, it doesn’t matter! Just talk to me, we can work this out. I know we can.”_

 

TO SAVE PRESS POUND, TO DELETE PRESS SEVEN: **7**

 

NEXT MESSAGE:

 

> _“Rory, hi! It’s Honor Huntzberger. I’m bummed that I couldn’t get you on the phone. I’ve been exiled. My parents house is eleven thousand square feet and smoking is banned from every nook and cranny of it. Only because Mom stopped smoking again. So, here I am, freezing my ass off. Anyway, I was just calling to tell you what a drag this is—you and Logan, I mean. When he said you broke up I almost threw lamp at him. Moron, he’s his own worst enemy. I was wondering where you were for New Years, and at first young Ryan Seacrest hemmed and hawed, which wasn’t sufficient. Idiot—him, not you! I’m so sorry but you and I can still go shopping you know? Bergdorf’s is calling… Well, I have to get back inside before I turn into an ice cube. I hope you had a nice holiday and I’ll be in touch! Bye Rory.”_

 

TO SAVE PRESS POUND, TO DELETE PRESS SEVEN: **#**

 

**AGE TWENTY-THREE. AUGUST. PHILADELPHIA**

By the time Rory was feeling confident enough to go out and talk to her mother the sun was getting ready to set.

It was almost nine o’clock at night, and Rory had done an incredible job of avoiding her mother in the tiny two bedroom apartment. She’d requested that Jess bring her food, water, and coffee and only left the room to use the bathroom. Jess talked to her mother sometimes, telling her that Rory would be out soon but she just had to be patient. Their conversation was mostly quiet murmurings and Rory couldn’t hear much, but her mother _did_ leave the apartment for quite a few hours to “clear her head” according to Jess.

She knew she should’ve talked to her mother sooner, she just didn’t have the energy. Jess tried to encourage her to do it before Matt and Chris got home, and so, finally, she pushed herself up out of bed and wandered into the living room. Jess followed her a few moments later, but he stayed in the kitchen and started to make them some dinner. He was close enough to step in if need be, but far enough away to give them space, too.

Her mother was watching television, curled up under a fluffy blanket, her blue eyes rimmed with red. Rory felt a pang of guilt. She hadn’t meant to make her mother cry, but there was also a twinge of annoyance—What did Lorelai Gilmore really have to cry about? Mom glanced at her when she sat down but she quickly turned back to the television, clearly not wanting to be the one to speak first.

Rory took a deep breath, centred herself, and then bit the bullet, “I’m sorry, Mom.”

Her mother turned to take in fully. “For what?”

“For yelling at you, for making you cry… For lying.”

“Okay,” Mom nodded stiffly. “I’m sorry, too. If I’m really as judgmental as you say then I pushed you into lying to me. I’ve been trying to come to terms with that all day.”

Rory pursed her lips.

“Rory, you made me out to sound like _my mother.”_

“You kind of are, sometimes,” Rory confirmed. She bit the inside of her lip when her mother looked at her in disbelief and hurt. “It’s just… You’ve tried _so hard_ not to be Emily Gilmore, that in a sort of cruel, tragic irony you really _can_ be just like Emily Gilmore. And, I know that’s hard for you to hear and I’m sorry, but Mom, _every time_ I do something you don’t like, you get controlling and mean. Have you honestly never noticed that?”

“No, Rory, I haven’t! I haven’t noticed that because I thought that our relationship was one built on mutual trust and respect! And now you’re telling me that I’ve been as harsh and cruel as my _own mother?”_

Rory looked down at her hands and swallowed hard; she hadn’t meant to hurt her mother’s feelings, but Jess told her that she should be open and honest with how she felt about everything in this situation and she knew he was right. “Mom, we can fix this. But we can’t fix it if you don’t know what there is to fix, okay? I’m telling you how I feel so that we can take the proper steps.”

“When did this begin? When did I all of a sudden start _acting like my mother,_ hm?”

“I don’t know,” Rory shrugged, looking at her mother incredulously. “You’ve _always_ done it, but if you want the biggest example then we have to rehash the Yale thing again. I wasn’t doing something in the way that _you_ wanted me to do it, and instead of supporting me and being my rock through it all, you abandoned me. You kicked me out, and you refused to see my side at all. In the end, I had to come running back to you only when I was living up to your standard again. I’ve thought about this so many times, and if I’d just had your support I probably would’ve went back to Yale _a lot sooner_. But you refused to support me when things really got tough, Mom, and it was all because I was living up to _your_ ideals of me.”

“Rory, we’ve talked about this! I’ve apologized numerous times!”

“It doesn’t change the fact that you made me feel stupid for my own life choices.”

“You let a man like Mitchum Huntzberger get into your head! You got a criminal record!”

Rory scoffed, crossing her arms over her chest. “Oh, please! You never once cared about the criminal record. Sure, you were mad but you didn’t kick me out until I was falling off the path of precious Yale University graduate on her way to working for CNN. You’ve always had a dream for me, and even though we are best friends, you put a ton of pressure on me to me what you wanted. Don’t you see that?”

“Rory, _you_ wanted to be a journalist!” Mom argued, looking angry now. “I _never_ forced you into that, at all! If you decided you wanted to be Bobo the Clown, I wouldn’t complain! But dropping out of Yale? Really? Come _on_.”

“I was hurt and upset. I needed my mother’s support, and I didn’t get it!”

She hadn’t noticed that their voices were raising until Jess cleared his throat in the kitchen. He stood behind the counter, staring at her with a slightly worried look, and Rory felt the fight drain out of her. This wasn’t the way this conversation was supposed to go.

“I don’t want to fight,” Rory said. “I just wanted to tell you how I felt, that’s all. I was hoping that once you knew, we could move past this. Can we move past this, Mom? Please?”

Mom shrugged, her jaw set up a little hard. “I don’t know.”

“Mom—“

“You make me out to sound like a monster—like a horrible mother!”

Rory sighed in frustration. “If I felt that way would you really be my best friend?”

“I don’t know, Rory. You _lied_ to me, and best friends don’t lie to one another. I’ve _never_ lied to you.”

“Really?” Rory asked, nose wrinkled in disbelief. “You’ve never lied to me? So when you hid Dad and Sherry’s Christmas card from me and told me he hadn’t called, that wasn’t a lie?”

Mom looked a little panicked then, her eyes wide as if she hadn’t expected Rory to bring up any of her past transgressions. “I came clean to you about that!”

“Yeah, after I _asked you!_ You didn’t come clean out of your own volition!”

“So, now I’m the bad parent and your dad’s a saint?”

Rory rolled her eyes. “You know I don’t think that.”

“I don’t know what you think of me anymore because according to you I’m a judgmental, lying Emily Gilmore reincarnation.”

“You’re being very dramatic.”

“Oh, I’m being dramatic!” Mom threw her hands up in the air. “Well, if I’m dramatic what does that make you, huh? Shacking up with your quote-unquote _best friend_ in the same bed for almost a year and never _once_ telling me about it. Unbelievable!”

“I already explained why I didn’t tell you,” Rory said, trying to keep calm. “I love Jess, Mom. You know that I love Jess, you’ve known that I’ve loved Jess long before _I_ knew I loved Jess. If I had told you about the situation, what would your reaction have been?”

“I don’t know, Rory!”

“Well, I do,” Rory argued. “You would’ve told me I was being stupid, shacking up with a guy I’m in love with who doesn’t feel the same way about me. You would’ve painted Jess in the worst light imaginable—which you proved the moment you turned on him when you found out the truth—and you would’ve done everything in your power to get me away from him, even though that’s not what I ever would’ve wanted. But I would’ve done as you asked because I would’ve been afraid of our relationship deteriorating!”

“So, again, this is all _my_ fault?”

Rory tucked a strand of hair behind her ear with a small sigh. She was not going to get upset and yell. “No, you’re not entirely to blame. I need to learn how to not care about what you think so much, but you’re my _best friend_ and _my mother,_ so I care—sometimes a little too much—about your opinion of me.”

“Rory…” Mom said, finally sounding like she got it. “I’m _sorry_. I don’t want you to feel like you can’t talk to me because you’re afraid of what I’ll say or how I’ll feel. You’re twenty-four, babe. Your life is yours and I should respect that and understand that, but you’re right, sometimes I don’t… I was just _hurt_.”

“I know,” Rory nodded, “and I’m sorry. I never meant to hurt you, and I really am so sorry for lying, I just… wasn’t ready to have _this_ conversation yet.”

Mom reached forward to grab her hand. “And he really didn’t try to sleep with you at all?”

Rory laughed and shook her head while glancing over at Jess with a warm smile. “Not even once,” she said, looking back at her mother. “He even made us sleep with separate blankets.”

“Wow. Maybe he really is as good as you and Luke say he is.”

“He is,” she confirmed. “He really is.”

“And you’re happy?”

Rory beamed. “ _So_ happy.”

Mom smiled back at her. “Then I’m happy for you… and I’m sorry for any pain I’ve caused you. I want you to know I’m going to work on the whole _judgmental_ thing, okay?”

“Thanks, Mom.”

“I love you, Kid.”

Rory moved in closer to lay her head against her mother’s shoulder, basking in the warmth of her mom’s arm around her back. “Love you, too.”

 

**AGE TWENTY-ONE. JANUARY. YALE/STARS HOLLOW**

Returning to Yale felt like a much needed breath of fresh air. If there was one thing that living with Richard and Emily Gilmore taught her, it was that she wasn’t made to be stagnant. The DAR was fun and put her mind to use, but it wasn’t even remotely close to being in a classroom surrounded by her peers fighting over novels and politics. Besides, nothing could compare to the whirlwind that was the Yale Daily News either. Stepping back onto campus felt incredible, even if her new apartment was seedy and Paris was more manic than usual.

The only negative was Logan’s incessant pleas for her to take him back, and they really were incessant.

They’d fought over how he’d broken up with her via his sister and how Rory hadn’t called him back since their fight, but she pointed out that he’d asked her for the impossible. Her friendship with Jess was not something to be used as a bargaining chip, and he couldn’t try to control nor dictate her life simply because he was unhappy about their relationship. She’d never, not once, overstepped her boundaries with Jess. Sure, she got a little flirty when drunk, but Logan acted like she’d gotten down on her knees and sucked Jess off right in front of him or something.

She’d simply taken some time away from Logan for herself. That hadn’t meant that they were broken up. Of course, when she’d pointed this out to him, he’d told her that he hadn’t meant what he said to his sister at all.

“Honor was bugging me, and I just told her we broke up to shut her up. I needed some time,” he tried to explain as she moved into her new apartment.

“So, you didn’t mean it?” She asked, appraising him; she couldn’t tell if he was lying or not. Deep down she _wanted_ to be sympathetic to Logan and forgive him. He’d been calling her for months, trying to talk to her and she’d been cruel and cut him off at the kneecaps basically, but she had also needed some time, much like he did. But she loved him, oddly enough. She couldn’t explain why, just like she couldn’t explain why she’d fallen for him in the first place (he was so not her type), but she really did love him.

Logan sighed, shaking his head. “No, I did… I just… it was too much for me, okay?”

“It was a fight,” Rory said coldly, sympathy suddenly gone. “People fight. And you can’t have it both ways, Logan. You can’t say you just told your sister we were broken up to get her off your back and then turn around and tell me that you _did_ mean it. Either you broke up with me through your sister or you didn’t.”

“Yeah, well, I don’t fight. I don’t want to be screaming at you in a bar. I can’t take that. It’s too much drama for me.”

“If you can’t take drama then you shouldn’t even be in a relationship,” Rory explained easily. “Which, by the way, you’re not, so everything’s good.”

“It’s not that easy,” Logan said, and Rory fought the urge to scream. She just wanted him to leave her alone.

They bickered for a while and he tried to help her bring in her boxes, but she told him she didn’t need the help.

“I thought that I wanted to break up. I thought that it was a stupid experiment, me trying to be a boyfriend, that it didn’t work and I’d just move on. And I didn’t. Couldn’t, actually… Rory, I love you.”

Rory paused then, just for a beat. “I have an appointment, I have to go.”

She left him standing outside and locked the door immediately, rushing into her room feeling sick and dizzy. She fumbled in her attempt to find her phone in her bag, but she fished it out and dialled Jess’ number off by heart. It rang three times and Rory was scared he wasn’t going to pick up, until finally a voice came on.

“Hello?” It wasn’t Jess. She didn’t know who it was. It sounded like a woman though. “ _Helloooooo?_ ”

Rory bit her lip, snapped her phone shut and leaned back on to the couch, staring up at the ceiling blankly for a moment before she got ready for her mandatory counselling session. Thankfully, Logan was gone when she left the house, and the counselling session wasn’t quite as bad as it could’ve been—crying over coffee and Logan aside.

She’d called her mother immediately after to recount what’d happened, making jokes about padded rooms. Her mother asked if she believed that Logan really loved her, but Rory didn’t know. She hadn’t been kidding when she told her therapist that she was scared that one day he would love her and the next he wouldn’t. She really was expecting him to just show up with another Birkin, and she had no one else to rant to save for Lane.

That whole random-woman-answering-Jess’s-phone thing had thrown her for a very serious loop. She hadn’t even known that Jess was seeing anyone out in Philadelphia. He’d never said anything, and Lane certainly hadn’t alluded to anything either. So, then, who was that woman on the phone? It was bothering her more than she cared to admit, so she forced herself to focus on Logan and his declaration of love. Yes, she had told him that she loved him while living at her grandparents house, but things were different now. He’d asked her to leave Jess behind, Jess had almost broken his nose, and in the end Logan had broken up with her through _his sister._ Was a man like that even worth forgiving? No matter how much she loved him, she had to be pragmatic.

Rory remembered Jess’ look of judgment when he saw she wasn’t taking Logan’s calls, and the words that he’d said, but _she_ wasn’t the one in the wrong, Logan was! This situation bothered her so much that she was practically unable to focus.

In past week, Logan had pretty much stalked her. He’d even paid the coffee cart guy to follow her around. There was literally no escape from him at all, and he wasn’t listening when she said that she didn’t want to get back with him. He was relentless and honestly disrespectful toward her feelings.

Friday night dinner’s had yet to be reinstated after she left her grandparents house, but Rory still a bit of relief from Yale when she went home for the weekend anyway.

It was the Winter Carnival and she and her mother had volunteered to run a booth with Paul Anka. It’d been fun, until Rory witnessed Dean and Lindsay walking around the square, though neither of them looked happy. She didn’t mean to spy or eavesdrop, but their relationship had always been fascinating to her after her own break up with Dean, and she wondered just what it was like to be married at twenty-one. According to town gossip, the two of them weren’t doing so well, and Rory finally got to witness it first hand as they broke out into a fight by the hot chocolate booth.

Lindsay looked up and caught Rory staring, so Rory pretended to not have been looking, but the blonde stormed past her booth with a loud, “Figures”. Rory really didn’t know what Lindsay was talking about or why she felt such animosity to her, but she tucked it away and tried to be civil to Dean when he came up to talk to her when her mother left with Paul Anka to grab them some coffee.

“I’m sorry you had to see that.”

“Oh, that’s okay,” Rory said with a shrug, rubbing her gloved hands together to keep them warm. “Everyone has relationship problems sometimes. I’ve been there, too.”

“Yeah?” Dean asked, sounding a little disbelieving which Rory found funny.

She raised her eyebrows at him and gave him a wry smile. “You broke up with me at my grandparents house in front of my friends, remember?”

Dean winced. “Right. Sorry.”

“Water under the bridge,” Rory said simply. She meant it, too. It’d been a long time since she’d thought about Dean, and the grudge she’d been carrying had long dissipated in the two years they’d been apart. “Besides, I was talking more recently.”

“You and your boyfriend not doing well?”

“Well, let’s just say he is no longer my boyfriend.”

Dean looked down at his shoes with a smile. “Oh,” he said trying to suppress it, but she could still see it. “I’m sorry to hear that. Lindsay and I… we’ve been fighting about the past recently…”

Rory licked her lips; her attraction to Dean was still alive and well. He was tall, more muscular than he’d been while they were together, and his hair was a nice length for pulling on. She mentally slapped herself, unwilling to delve any further into her disturbing, sexually deviant thoughts. This was a married man, after all. It didn’t matter how many bombs he not-so-subtly dropped about still being into her, she couldn’t be the other woman. What would her mother say?

“We’re actually thinking of getting divorced.”

She bit her lip then and questioned God on why he was testing her. “Are you sure that’s a good idea?” She asked, fidgeting on the spot. “I mean, you could try counselling?”

“We’ve tried everything, Rory. She just doesn’t make me happy—not the way you used to. Look, I was hasty back then, I shouldn’t have broken up with you… I never,” he sighed and shrugged, “I never really got over you. And now you’re single and we’re here and it feels a bit like fate, doesn’t it? Lindsay knows I’ve never gotten over you. I still have so much of your stuff and sometimes she’ll catch me looking at pictures of us… I don’t mean to dwell on the past, it’s just… you were my first love. Maybe, even my only love.”

His words were pretty and they made Rory feel kind of warm and gooey inside, though Dean was always good at making her feel that way. If she had to describe her relationship with Dean, then she would’ve described it as safe. He was mostly kind, usually dependable, and he loved her. He could wrap her up and swallow her completely in those arms, and even though she knew it was wrong, she kind of wanted to feel that again.

“Could we maybe… talk somewhere more private?” He asked hopefully. “I have so much more I’d like to say to you.”

She had nothing to lose, anyway.Jess had some woman answering his phone, Logan was being… well, Logan. She was single. Dean was here and going through a divorce, and to put it simply—she was curious.

“Yeah, sure… Just, um, give me five minutes,” Rory told him just as she spotted her mother and Paul Anka coming over from Luke’s.

 

**AGE TWENTY-THREE. AUGUST. PHILADELPHIA**

Rory and Lorelai spent the rest of the night watching movies and catching up on old television shows. Jess had been secured as their personal errand boy after Lorelai personally apologized to him for her assumptions and attack on his personhood during dinner. Jess had forgiven her kind of easily; he still wasn’t exactly Lorelai Gilmore’s biggest fan, but Rory _and_ Luke loved her, so he’d put those feelings of teenage angst long behind him.

Matt and Chris had come home just a little after Rory and Lorelai had made up. Matt decided to give up the sofa-bed for Lorelai and shacked up with Chris for the night. Jess wound up having his bed to himself when Rory fell asleep in her mother’s arms with the television still on, surrounded by an unhealthy amount of snack wrappers. It felt weird to sleep alone. He wasn’t used to it anymore, and he missed the feeling of Rory’s nose pressed into the side of his neck. But, still, he stretched out and tried to enjoy the free space.

When he woke up the next morning, the mother-daughter duo were still fast asleep, Matt was making breakfast, and Chris was sitting at the counter with his laptop.

“Gooood morning,” Matt said happily as he turned out some scrambled eggs onto a large serving plate. “Your girlfriend and her mom are straight up _adorable_. How does a girl so pure have sex with a man so sinful?”

Jess rolled his eyes and took a seat next to Chris. He glanced at his computer screen out of the corner of his eye but turned to focus on it when he saw what looked like apartment floor plans.

Chris looked at him, eyebrows raised in a gesture that Jess couldn’t really decode. “It’s about time, no?”

“I guess.”

The whole thing made him feel a little morose. Since he’d made it out to Philly, it’d always been him, Chris, Matt and Austin, but then Austin got his own place, and the three of them had decided to move in here when the apartment above Truncheon became inhabitable. To see Chris looking at a place of his own made Jess’ heart sink a bit, even if he did agree that it was time for them to all go their separate ways—or at least some of them. Jess and Matt were going on twenty-five and Chris was going on twenty-six, they couldn’t live in a two bedroom loft forever.

“I’ve been thinking of moving out, too,” Jess admitted, more to himself than his roommates. It’d been something he’d been ignoring for a while now, but the idea kept resurfacing in the back of his mind every so often. Rory had brought it up once or twice, too, but the longest conversation they’d had about it had taken place yesterday while she wasn’t talking to her mother.

 _“Don’t you think it’d be a good idea if I moved out?”_ She’d asked, looking pensive. _“This was always supposed to be temporary, anyway. And then you, Matt, and Chris can go back to the way you were.”_

He’d entertained the thought for her, but he hadn’t been able to come up with a good reason why she _shouldn’t_ get her own place that didn’t include him getting selfish. Did he want Rory to move out? No, not at all. He desperately wanted her to stay with him now that they were finally on the same page, but he knew they were only living together out of circumstance. Their relationship was barely even two months old, and he didn’t feel right asking her to move in with him _like that._

In the end, he’d decided that maybe it was best for the both of them to just get separate places.

“Yeah?” Chris asked, bringing him back to the present. “Well, I mean only _one_ of us would have to move out and then it’s fine. We’re just getting a little overcrowded is all.”

Jess nodded in agreement. “Rory’s going to get her own place soon, and if I move out then Matt can just take my old room.”

“You and Rory are going to move into together?” Matt asked, setting down the finished breakfast on the counter—eggs, bacon, toast, and orange juice.

“I doubt it,” Jess said, grabbing a plate from the stack that Matt put down. “She’ll get her own place and I’ll get my own.”

“Cool,” Chris said. “Lane was saying something about possibly moving to Philly actually.”

“Really? She never said anything to me. I don’t even think she told Rory…”

Chris bobbed his head a little noncommittally. “Yeah, I don’t know it was just a small talk we had. She was saying that the band has really been struggling for years without Zach, anyway.”

Jess grunted at mention of that man’s name. “Well, a change of scenery wouldn’t hurt her.”

“Definitely. Maybe she and Rory could even move in together?”

“Yeah,” Jess shrugged, “Maybe.”

The topic of moving out and Lane and Rory had been stowed away over breakfast as they settled into a brief conversation about Truncheon book sale numbers, Zine publications, and Jess’ rapport with his newest author, a young college student named Nita.

Rory and Lorelai woke up somewhere in between Jess telling Chris and Matt that Nita’s manuscript was looking good so far, but it was a little rough around the edges. Rory interrupted his conversation to give him a kiss before she headed off to the bathroom, and Lorelai leaned against the counter and shoved some bacon into her mouth as Matt rushed out of his seat to make her some fresh coffee.

“Bless you, my son!” She cried out to him. “Why couldn’t my daughter date you instead!?”

Matt mumbled an, “I wish” and Chris sniggered while Jess rolled his eyes.

When Rory came out of the bathroom, still dressed in her pyjamas she found a seat on Jess’ lap and ate the remainder of food on his plate as Matt handed her a hot cup of coffee. Jess laid his chin on his girlfriends shoulder and placed a small, chaste kiss to her shoulder which caused Lorelai to hiss.

“Bad, nasty cousins!” She said, covering her eyes and Jess placed another kiss on Rory’s skin in defiance.

“If you think that’s bad just wait until you…” Chris trailed off as Jess and Rory both shot him a glare. “Never mind.”

“Good boy,” Rory praised, reaching over to pat him on his back. “No scarring my mother while she’s here.”

 

**AGE TWENTY-ONE. JANUARY. YALE/STARS HOLLOW**

“I’m a horrible person!” Rory cried, rushing into Lane’s apartment with tears in her eyes. “I’m a dirty, disgusting, horrible, awful person!”

“Okay, slow down here,” Lane said, closing the door and pushing Rory into her bedroom where Zach and Brian couldn’t hear them. Zach looked slightly intrigued by Rory’s words, but Brian looked straight up horrified. She locked her door and put a pillow against the bottom frame so that their voices wouldn’t carry. “What happened?”

“I slept with Dean!”

“You what!?”

“At Miss Patty’s!”

“Rory!”

Rory covered her face with her hands. “I know! I’m awful!”

She felt the mattress sink as Lane sat down next to her. “How did this happen?”

“I don’t know,” Rory said miserably as Lane gently removed her hands from her face, Rory didn’t fight her. “He saw me at the carnival. He and Lindsay got into a fight and then he told me that they were getting a divorce and he always loved me, and I told him we’d talk somewhere more private. I didn’t think I’d sleep with him!”

“Oh, Rory…”

“I mean I was thinking about it if I’m going to be honest, but I thought I had better morals than that. We decided to talk at Miss Patty’s because no one was there and it was quiet, and next thing I know we’re discussing our lives and our feelings about things and I got upset because Logan’s a jerk and Jess didn’t pick up the phone and so when Dean kissed me I didn’t fight it! All of a sudden my clothes are off and I’m having sex with my high school ex on the soft mats!”

Lane was quiet for a beat before she simply said, “Wow.”

“I know! I’m awful!”

“What about Logan though…? I thought you two were together?”

“We _were_ until he broke up with me through his _sister!”_

Lane gasped. “You never told me about that!”

“Yeah, well, he did. And then he shows up at my apartment and tells me he _loves me_ and that he wants me back! Why should I take him back?! I didn’t even know we were broken up in the first place. He even hired the coffee cart guy to follow me around!”

“Oh my god, awww.”

“No, Lane!” Rory argued, shooting her a dirty look. “No _awww_ ’s for Logan, okay? I don’t want to be with him.”

“Right,” Lane said, sounding easily convinced. “So, you want to be with Dean now?”

“No,” Rory said, but then she thought about it and it didn’t seem quite _so_ bad. The sex was decent, not better than Logan, but better than it’d been in two years ago. “I don’t know… Dean’s just so _dependable_ and _safe_. Unlike Jess or Logan.”

“Whoa, Jess?” Lane asked and Rory blushed. “I didn’t know Jess was a factor.”

Rory shrugged, trying to stay cool. “He’s not.”

“Do you still have feelings for Jess, Rory?”

“I’ve never _had_ feelings for Jess, Lane! I _thought_ I had feelings for Jess, and sometimes when I’m drunk I slip into old habits. That’s not the same a having feelings. He’s just very handsome. I mean have you seen him? Can you blame me?”

Lane snorted. “I try not to look at Jess in that light… he’s more like a brother.”

“Ew.”

“So, wait… you said you called Jess and he didn’t pick up the phone? What does that have to do with sleeping with Dean?”

“Nothing.”

“Then why’d you say it?”

Rory leapt off the bed to pace around her friends room. “I don’t know, Lane! I called him, some girl picked up his phone instead and I hung up.”

“Oh,” Lane nodded. “That’s why you’re upset.”

“No! I’m upset because I slept with Dean who is _married_ , it doesn’t matter if he’s going through a divorce right now, he’s _still_ married! My mother would hate me if she found out.”

“Rory, breathe, it’s okay. You’re upset about a lot of things right now—Jess, Logan, now Dean. It’s a lot for anyone to handle.”

“He just made me feel so safe, you know? Like everything was going to be fine, that this was all _meant_ to happen. He kept saying it was fated and somehow that sounded super romantic to me? Ugh! Who am I?! Who have I become? I thought I fixed everything!”

“It’s _okay_ to still have feelings for Dean, Rory.”

She bit her lip, wondering if what Lane was saying was true, and wondering if she even _did_ still have feelings for Dean or if she was just using him to fill the current hole in her heart. Logan had hurt her and Jess was back in Philly. She was vulnerable, and she’d let Dean get his way. “I don’t. I don’t have feelings for Dean.”

“Well, then why sleep with him?”

“Because I’m horrible, don’t you get it?!” She finally sat back down on the bed and covered her face with her hands again.

Lane rubbed gentle circles on her back. “You’re not horrible, Rory. You’re just sad right now is all and sometimes when we’re sad we do things we normally wouldn’t do. Like sleeping with our ex in a semi-public place.”

Rory laughed, though it came out more like a sob and Lane rubbed her back a little firmer. She let her hands drop from her face and she took a deep breath. “I’m going to tell Dean that we can never do that again.”

“That’s my girl!” Lane cheered. “I believe in you!”

Rory stood up from the bed and gave Lane a tight hug. “Thanks, Lane. Wish me luck.”

“You don’t need luck, you’re Rory Gilmore.”

She laughed then, wishing that were true.

 

**AGE TWENTY-THREE. AUGUST. PHILADELPHIA**

Jess was actually very glad to see Lorelai go. He knew Rory was sad about it, but the apartment was starting to feel cramped. He spent most of his time out of the house only because he couldn’t take the energy within it. Truncheon was running fine and there wasn’t much for him to do other than edit manuscripts and help people in the store if their other employees were busy with inventory or something. Work had been his main excuse to have some much needed time to himself, and he hadn’t even been a little sad when he got home and Lorelai was already on her way back home.

The only shitty thing was that he was dealing with a very mopey Rory Gilmore.

“I miss her,” she said, pouting.

“I know.”

Rory sighed, snuggling up closer to him in bed. “But it is nice to sleep with you again. Did you miss me?”

He smirked at her childish question but didn’t answer it just to tease her.

She pinched his side and he glared down at her. “Answer the question, sir.”

Jess shifted to capture her lips between his quickly.

“Are you sick of me already?” She asked, pout back in full force.

He held back a laugh and kissed her again, deeper this time.

Rory hummed in appreciation. “Pretty good answer,” she said before dragging him back down to kiss him again. She rolled on top of him and straddled his hips in that way she knew he liked. He grunted as she ran her fingers up his shirt and dug her nails into his flesh. Rory grinned against his lips and slid down his thighs to pull at his boxers.

“Let’s play a game called _how quiet can you be_ ,” she teased, rubbing her hand over his growing erection. He felt the cool air on him the moment Rory pulled him free of his underwear, but she quickly took his half-hard member into her mouth and swirled her tongue around the tip and then licked up from the base to the tip a few times.

Jess took in a sharp breath as Rory took him in all the way. His hips jerked up, but she held him down with her hands before letting him go with the drag of her tongue. “No moving,” she told him before taking him into her mouth again. She bobbed her up and down his length in a slow, torturous pace that Jess staring up at the lights on their ceiling and clutching the sheets so that he didn’t just completely take over.

She tightened her pressure around him and moved a little faster, enough to get him quietly panting. Rory clutched at his hips with her fingers so hard that he’d probably be sore tomorrow, but he definitely wasn’t complaining. He liked it when she got assertive like this. Finally, she started sucking him at just the right pressure and speed, but just when his pleasure would build and he started to moan, she’d let him go completely with a giggle.

“Stop torturing me,” he demanded, glaring down at her.

Rory pumped him nice and slow with her hand and gave him an innocent smile that didn’t match what she was currently doing. “But I like it.” She didn’t give him the time to respond before she took him into her mouth again and continued at the same speed and pressure that he liked. He rolled his hips without meaning to and she pinned him down again, relentlessly sucking.

“Oh, god,” he panted.

Rory hummed against him and the vibration almost brought him over the edge with a loud moan that he was sure Chris and Matt could hear. She pulled back just before he came and squeezed him to stop him from orgasming.

He groaned in frustration at her antics and yanked her up to him to kiss her. “You’re a tease.”

“I just want you to fuck me and I don’t want to have to wait five to ten minutes.” She smiled at him.

“Hey, my turn around time is pretty damn good.”

“I agree,” she said against his lips. “I’m just impatient.”

Jess licked his lips and pulled Rory’s camisole off her of her before taking one of her nipples into his mouth, tracing her areola with the tip of his tongue. Rory arched her back to give him better access and he kneaded her other breast with his hand, tugging on her nipple until it was taut and then he let go of the other breast to suck her left.

Rory ran her fingers through his hair and tried to wiggle of her underwear.

“Leave it on,” he told her, kissing his way down her stomach before sitting up to flip them over. He rubbed her through the wet cotton and pulled them to the side. Jess dipped a finger into her and appreciated the easy slide and the way Rory moaned at the contact. “Turn on to your stomach.”

She did as she was told and Jess pulled her underwear down slowly and let it rest on the middle of her thighs. He grabbed her some pillows and made sure she was comfortable before grabbing a condom from his drawer, slipping it on and lining himself up with her from behind. Jess slowly pushing himself in until his pelvis was pressed firm against her ass, moaning when she squeezed him on purpose and smiled back at him.

He thrust in and out about as slow as she’d caressed him earlier, and he watched as she shoved her face into the pillow to muffle her moans. Jess continued on like that for at least two minutes before Rory turned back at him with a glare.

“Jess. Go faster.”

“But I like torturing you,” he teased, repeating her words from earlier.

Her blue eyes rolled into the back of her head as he picked up the speed a little bit, and she bit her lip and let out a happy moan. Jess felt a jolt run down his back at the sound and he pushed a little harder and a little faster, causing Rory to moan louder, never once removing her teeth from her flesh. He placed his hands on her hips and curled his fingers around her to push her down into the mattress as he fucked her with slight abandon, his breathing laboured as he unintentionally picked up the pace.

“Just like that,” Rory encouraged and she slipped a finger into her mouth, eyes closed as her body rocked back into his.

Jess loosened his hold around her and balanced himself over head with his two hands, dragging himself out higher and faster and slamming back in harder in a way that had Rory squeaking almost as high pitched as their bed frame. Sweat rolled down his temples and to his chest as he snapped his hips forward hard and fast, the sounds of his pelvis hitting her from behind was loud.

Rory was biting the pillow and her words weren’t making any sense.

Jess twitched inside of her and announced his incoming orgasm, which Rory moaned louder at and she lifted her hips off the bed a little to reach down and rub herself as he came. She came soon after and he kept up his thrusts to increase her pleasure until her legs stopped shaking and her body relaxed. Jess pulled himself out and took off the condom, throwing it into the trash bin by their bed and collapsing next to her with a deep breath.

“You think Matt and Chris hate us right now?”

Rory giggled. “Definitely.”

“We should take up Matt’s suggestion and get a sex playlist.”

“Sounds good to me,” she said, laying her head on his shoulder and sighing happily.

 

**AGE TWENTY-ONE. JANUARY. STARS HOLLOW**

Dean showed up at her house on Sunday an hour before her mother got home from work.

Rory hadn’t necessarily invited him over. She’d given the situation a lot of thought and planned on asking him out for coffee when she was back at school. That way they could meet up half way, in public, and she’d make a clean break, but Dean had never let her do anything according to plan. He stood at her back door looking happy holding up a bottle of wine.

“Surprise,” he said and he kissed her, though she didn’t kiss back—not that he noticed. “I know you have to go back up to Yale tonight, so I thought I’d come and see you before you go.” He moved past her to put the wine on the table, and Rory stared at him, feeling a little dumbfounded.

Dean wrapped his arms around her waist and leaned down to kiss her again, but Rory wriggled free of his grasp and held her hands out for him to stay away. “I can’t do this,” she said, feeling sick to her stomach. “I know you said you and Lindsay are going through a divorce, but this still feels _wrong_. You’re still technically married, Dean, and I can’t _be_ with a married man.”

He looked confused. “You weren’t saying that last night.”

“I know, but… I was sad and lonely and you always made me feel safe, so one thing led to another but it wasn’t my intention.”

“Sure didn’t seem that way when you took me into Miss Patty’s.”

“Miss Patty’s is not a place to have sex, Dean!”

Dean didn’t really seem all that fazed by her feelings on this. He was smiling at her as if he found her outburst cute, but she didn’t think any of this was cute or funny at all. “Come on, Rory. We had a good time, didn’t we?”

“W-well, yes, but that’s not the _point_.”

“Isn’t it? Rory, come _on_. You had a good time judging by those sounds you were making…”

“Dean…”

“Rory, I _love_ you. This isn’t a game to me, don’t you want to be with me?”

She knew the answer to that, but she didn’t want to hurt his feelings. “You’re married.”

“Yes, but I’m getting divorced!”

“Do you even have a lawyer? I mean, you still wear your ring… I noticed it last night.”

Dean held up his hand and removed his ring for her to see and placed it down on the kitchen table. “Rory, when I say things are over between me and Lindsay, I mean it. You’re the only girl I’ve ever loved. You’re the only one I want to be with at all. Don’t you see that? My marriage was destroyed because I was so miserable without you, and I thought that last night we were finally on the same page…”

Rory didn’t know what to say, and she didn’t know what to do when he came closer to her and wrapped his arm around her waist, holding flush to his body. “Dean,” she tried to say but he cut her off with a kiss that made her mind go a little fuzzy. When he broke the kiss, her slid his hands up her shirt and gripped at her flesh. “We shouldn’t…”

His hands stilled for a moment but then he was kissing her again. Dean pushed forward and Rory stumbled back until they were in her bedroom. He laid her down on the bed and pushed her shirt up, exposing her bra and whatever complaints she’d been thinking before completely went out the window the moment he took her bra off and started tweaking her nipples. He’d always been kind of good at this part, really, so she let herself enjoy it.

All she could hear was her blood rushing as she grabbed for the hem of his shirt and pulled it up over his head before dragging him down on top of her, her legs spread open wide so he could fit between them. Her bed was too small for this, but she wasn’t about to start complaining now. Rory pushed her hips up against his jeans and moaned at the friction, and the sound of her pleasure must’ve drowned out the sound of her mother coming in the house because Dean leapt off of her quickly once Lorelai screamed.

“What the hell is going on in here!?”

“Mom!” Rory screamed, covering her naked chest with her hands.

Dean stood awkwardly behind her, frozen in place.

Her mother picked up Dean’s shirt from the floor and threw it at him. “Get out of my house,” her voice was terrifyingly cold, and Dean didn’t move an inch. Rory watched her mom’s face ripple in anger before she screamed, “Now!”

Dean seemed to snap right back into motion as he pulled his shirt on, grabbed his coat off the chair and rushed out the backdoor. The only sound between them was the echo of the door banging. Rory searched around for her shirt, and quickly put it on, avoiding her mother’s gaze.

Rory didn’t know how long they sat in silence for, but she knew she needed to say something. “I… didn’t mean for you to see that.”

“How long has this been going on?” Whatever anger her mother had toward Dean, seemed to have been completely washed away. It just seemed sad and disappointed.

“Since yesterday. I swear, I didn’t know that this was going to happen. I didn’t know he was going to show up tonight and it just… happened. It’s awful for you to find out like this, I know. I’m sorry. I didn’t even _want_ to sleep with him just now but I got caught up in the moment and I know that’s not an excuse, I just… I don’t know!”

Mom sighed, her arms crossed over her chest as she leaned against the doorjamb. “But… he’s married.”

Rory swallowed. “I know, but it’s complicated… you don’t understand the situation.”

“Is he still married?”

“Yes, but…”

“Then I understand the situation.”

“It’s not working out between them,” Rory explained, feeling sick to her stomach at the way she was trying to justify this, but she was just telling her mother what Dean had told her. “They’re not happy.”

“Oh, Rory…” Mom said, sounding extra judgmental. She pushed herself up from the door to walk around he daughters room and take in the scene. “He told you that? They’re getting a divorce? He’s got a lawyer? They’re dividing up the monster truck season tickets?”

“He said they’re getting a divorce, yes. I asked him about the lawyer and he… definitely deflected, but he said its over and that they both know it and they’ll be divorced soon.”

“It’s not over until he’s out of the house with the ring off.”

“He took the ring off!” Rory said, pointing to the counter where his ring still sat. “He’s in love with me, not Lindsay.”

“Does Lindsay know that?”

Rory faltered, thinking back to the fight she saw them have and the way Lindsay looked at her when she walked by. “I think so… but she’s not good for him, okay? She makes him quit school and work himself to death and —”

“No, Rory,” Mom shook her head. “Nuh-uh. You can’t be one of those girls who blames the wife for forcing the husband to cheat.”

“He wasn’t cheating,” Rory tried to defend, but she knew her mom was right.

“He was cheating, Rory. He was cheating and you were cheating with him. There’s no other way to spin that, kid!”

Rory huffed. “I’m not spinning it, and I’m not a kid! I’m twenty-one,” she said, voice cracking as she felt herself on the verge of tears now. “I didn’t mean for this to happen… I said no. I was trying to say no.” She finally broke down then, sniffling as she wiped at her eyes. “He wasn’t listening and my brain just shut off. You’re right, I’m stupid!”

Mom sighed and took a seat beside her on the bed. “Rory, you aren’t stupid… He took advantage of you because he could tell that you were sad. I always said Dean was the nice one, but I think something’s changed in the two years you’ve been apart. He’s not the same guy, or maybe he is and I just never saw his true colours before…”

“I was going to tell him we couldn’t do it again in a cafe far away from here, but then he just _showed up_ with a bottle of wine! And I don’t know, things with Logan just got me feeling so awful that it felt nice to be wanted for by someone and I didn’t _think_! I didn’t think at all!”

Mom ran a finger through her bangs affectionately. “I know, Babe,” she soothed. “You love and miss Logan, and being without him has been hard on you… but maybe you should forgive him, huh? If being away from him makes you feel this unsure and this lonely, then maybe he’s your person. You saw me when I was without Luke, I couldn’t even bring myself to get out of bed.”

“Logan would hate me if he knew.”

“Logan _loves_ you, hun. He told you that, and unless you have feelings for Dean again, then I think it’s possible you might love Logan, too.”

“I told him I did,” Rory admitted. “Back when I was at Grandma and Grandpa’s. I told Logan I loved him and I said he didn’t have to say it back, because I knew after the whole Dean experience that being pressured to say it back could lead to issues. And then he finally tells me he loves me, but it’s tainted by a fight with Jess, months of no talking and a break up via Honor Huntzberger.”

“So, maybe, if you love him you might want to give him a second chance, huh? Get off of this self-destructive path this breakup has put you on.”

Rory nodded, taking her mother’s words into consideration. “Yeah… maybe.”

 

**AGE TWENTY-THREE. AUGUST. PHILADELPHIA**

“Maria Maria is a great song,” Rory argued, “and I would totally make love to you to it.”

“We’re not having sex to Maria Maria,” Jess said, glaring at Rory from the corner of his eye. His laptop was resting on his thighs as he scrolled through his and Rory’s shared itunes library. They were trying to craft a sex playlist together, though their music tastes had a tendency to clash somewhat often.

Rory pouted at him. “Fine, but _Rock the Boat_ by Aaliyah is a must.”

“I’m just gonna wind up thinking about her and then I’ll get sad.”

“Aww,” Rory cooed, stroking his cheek. “Sensitive boy.”

Jess sighed. “Fine. Put it on the list.”

“It can be our love making song!” Rory said a little too excitedly, and Jess rolled his eyes.

“ _For tonight you’re only here to know_ by The Distillers?”

“Duh!”

“ _Speed of sound_ by Coldplay, too?” he asked, eyebrows raised in excitement.

Rory looked at him as if he had two heads. “No! No Coldplay!”

“Oh, come onnnnnnnn,” he complained. “I put Aaliyah on here for you even though all I’m going to think about is how she died. You can do some Coldplay for me.”

Finally, Rory gave in with sigh. “ _Finnnneeeeeeee._ ”

He kissed her cheek in gratitude just as Chris poked his head into their room. “Hey, what’cha guys doing in here? The door was open so I know it’s not sex.”

“I wouldn’t be so sure about that.”

“Shut up, Jess.”

“We’re making a playlist so that you guys don’t have to listen to us anymore when we… you know, do _it_ ,” Rory explained, blushing a little bit as Jess snickered at her wording.

Chris nodded, looking a little impressed, his mouth pressed at the corners. “That is actually very appreciated. Can I give you suggestions?”

“No,” Jess said at the same time that Rory said, “Yes.”

He rolled his eyes as Chris came in and sat on the edge of the bed near Jess. “Okay, so what do we have so far?”

“ _I will possess your heart_ by Death Cab, _Speed of Sound_ by Coldplay, _Rock the Boat_ by Aaliyah, _For Tonight You’re Only Here to Know_ by The Distillers, _Slow Motion_ by Juvenile, _The Guns of Brixton_ by The Clash, _Love Lockdown_ by Kanye West, _Sex on Fire_ by Kings of Leon…”

“What the fuck, no _Juicy_ by Biggie?” Chris asked, sounding disgusted with them. “At least _Hypnotize_.”

Jess thought it over for a second and nodded. “I could do _Hypnotize_. You?”

Rory shrugged. “Sure.”

He found it in their library and dragged it to their playlist.

“This is so great,” Chris said, grinning super wide. “Now when you two are getting nasty, if I hear any of these songs I know to leave the house and don’t have to wait for Rory’s extremely loud moans of your name.”

Rory spluttered beside him. “I’m not that bad!” Chris and Jess both threw her a look. “I’m not!”

Chris snorted. “I can literally record you if you’d like.”

“No thanks,” Rory said, blushing.

“Mmmmmhm,” Chris said easily, glancing back at Jess’ laptop. “Okay, so obviously some Lil Kim is a must. _Crush on you_? Classic.”

Jess glanced at Rory out of the corner of his eye and gave her a little smirk as she intertwined their fingers and laid her head on his shoulder, enjoying the rest of their lazy morning as Jess scrolled through their music library to Chris’ enthusiastic suggestions.


	12. Chapter 12

**Notes for the Chapter:**

> Hi, yes, I'm alive. Just suffering from seasonal depression lol so, sorry for the delay.
> 
> Uh, sorry if there's a ton of mistakes I literally didn't proof read it at all since I just wanted to get it up and out for you guys.
> 
> I hope the next chapter doesn't take me as long, and I apologize if this chapter is scattered or weird in anyway. As always, leave me a comment to tell me what you think! Thank you for reading!

**AGE TWENTY-ONE. APRIL. YALE**

If there was one thing Rory Gilmore couldn’t stand, it was dishonesty. And yes, she knew that was hypocritical considering how many white (and not-so-white) lies she’d told in the past, but she was _working_ on that.

When she took Logan back, she thought they were on the same page. She’d come clean about her misdemeanour with Dean Forester, and Logan had been more than understanding. She’d figured if he had any transgressions, he would’ve used their moment of truth to admit to them and they could move on. Instead, Logan had stayed silent and let her find out from the lovely bridesmaids themselves.

Logan said they were vipers, gossipers, all sorts of mean things, but the way Rory saw it was they were his victims. Logan Huntzberger didn’t know how to be a boyfriend, just like Rory’s mother had warned her, and now she was paying the price. Her anger was through the roof, and Logan refused to let her be entitled to it. He said things like:

“C’mon, Ace. I didn’t get mad at you for the Dean thing.”

And she’d pointed out that the only reason he hadn’t gotten mad was because he _knew_ he’d done something much, much worse and he hadn’t even come clean about it.

He also said, “I stuck with you even after the Jess thing, too.”

Which, made her even _more_ livid, because yes, she had made a mistake there too, but it’d been a drunken one and at the end of the night she’d picked Logan, anyway. But, Logan was Logan and he was relentless in the idea that Rory had to forgive him whenever he said she had to. And, of course, she was weak so she gave in every single time. His words made sense and he used logic to run around her so fast until she got dizzy and collapsed, but that _never_ changed the way she felt in the end.

They’d been fighting for months now and their home was tense and uncomfortable—only made worse by Logan finding Jess’ open house invitation in the mail.

“He’s my best friend, _of course_ he would invite me,” she’d said, rolling her eyes. “I doubt I’ll even go, I’m swamped with work.”

It wasn’t entirely a lie. She was swamped with work—essays, readings, being the editor of the Yale Daily News. She wanted to go out and see Jess desperately, but she wasn’t entirely sure if life would let her. Then, Logan found the letter and he started in on that. She’d come home after a long day to find him at the kitchen table, Christmas card in hand, and he read aloud as soon as she walked through the door.

“ _I just wanted you to know that I love you, too,_ ” She remembered Logan reading, sneering in his obvious disgust. “ _Those words have never been easy for me to say, but writing them down is a little easier._ Really, Rory? You tell me about Dean but you leave _this_ out? _And no matter how many arguments we have whether it's over books, or our significant others, Yale, whatever it may be... there's nothing in this world big enough to come between us. I sincerely hope you feel the same._ Wow. Okay.”

“Where’d you get that?” She’d asked him, but he just flicked the card onto the table and it landed right next to The Subsect.

“Thought I’d give your boy’s novel a try. Found that instead.”

Rory had bristled, suddenly feeling defensive. “You went through my things?”

“I was trying to be a good boyfriend. You kept going on and on about how he wrote a book and how proud of him you were for it, so I thought I’d read it! Didn’t know it was harbouring some big secret. You know, you say you’ve forgiven me for the bridesmaids thing but you haven’t. You say you’re not into Jess, but you are. Maybe you need to distance yourself from him, not for me, but for your own good, huh?”

There had been no words to defend herself with, so after Logan had made it clear that he needed “some space” and was heading off with the Life and Death Brigade for their last big _hurrah_ before graduation, Rory packed a bag and headed off to Philadelphia.

She hadn’t told Logan about the letter because there was nothing to tell. She’d told Jess that she loved him in a message and he’d repeated it back to her through a letter. They were best friends, and it wasn’t the big love admission that Logan seemed to believe it was. If he was going to be so disrespectful to go through her things, lie to her face about the women he slept with while apart, and then turn her into the bad guy, well then she didn’t need to be at home waiting for him to return.

Rory loosened her grip on the steering wheel a little bit as the road signs told her there was less then ten minutes to Philadelphia now. She took a deep breath and prepared herself for seeing Jess.

 

**AGE TWENTY-THREE. SEPTEMBER. PHILADELPHIA.**

“So, I know I said that it’d be best for me to get my own place and for you to get yours but I’ve been thinking about it and maybe we really _should_ just move in together?”

Jess and Rory spent the whole beginning of September apartment hunting, and they’d solidified one for Rory but they were still in the process of finding one for Jess. He’d have been lying if he said he wasn’t starting to get frustrated, but he knew finding the right place to live would take time and be a process. Patience was not his middle name, but he was doing his best to rebrand himself.

“I don’t think that’s a good idea,” he said easily.

At first it’d been him who was a little skeptical about moving into a separate place, but the more he thought about it, the more it made sense. They hadn’t been dating all that long, and sure, they’d been best friends for _years_ but if things went belly-up dating wise, at least they’d have their separate spaces. He wasn’t trying to jinx his new relationship, but he also wasn’t trying to trap himself and ruin a decade long friendship.

“Why not? I mean, we’ve been best friends for a really long time, we’ve been living together and sharing a bed already for almost a year. Just seems kind of silly to want space after everything, don’t you think?”

Jess shrugged, not wanting to hurt her feelings. “It’s not necessarily about wanting space or wanting to get away from you, it’s about being realistic. Yes, we’ve been friends for a long time and now we’re dating, but that doesn’t mean we should rush into anything.”

“But Jess—“

“Plus,” he said, throwing her a look, “Lane wants to move here and she _definitely_ is not ready to be living with Chris. Zach was different and also a bad experience that she shouldn’t be trying to relive or recreate. If she moves here, living with you would be best. She’ll just get upset if I’m there, too.”

Rory rolled her eyes. “Oh, she will not. Lane loves you.”

“This isn’t about who loves who, this is about relationship dynamics. You and I can barley keep our hands off of each other.”

“Are you complaining?” Rory asked a little snippily. She crossed her arms over her chest and glared at him. “Because _you’re_ just as handsy as I am, but if it’s such a problem I can clearly stop.”

“Oh my god,” Jess groaned, rubbing at his forehead as he walked into the kitchen.

“What?!” Rory asked, following him with flailing arms. “I’m just trying to understand!”

“I don’t have an issue with you being handsy, _obviously!_ The issue is that _Lane_ takes issue with us being handsy! I promised not to subject her to that again. I’m trying to keep my promise.”

Rory pursed her lips into a thin line. “You do know we’ll have our own room, right?”

“We have our own room here and Matt and Chris still complain.” Jess opened the fridge door and grabbed a bottle of water before looking for something to make for dinner.

“In lighthearted fun!”

Jess moved one of the juice cartons to the side to grab some sliced chicken that he’d hidden from Chris earlier in the week.“Matt found your bra in the couch, do you really want that to be Lane?”

Rory seemed to have deflated at that because he caught sight of her pout just as he closed the fridge door, his arms full with sandwich making supplies. “No…” She said miserably, “I guess not.”

He dumped the supplies onto the kitchen counter and took Rory’s face in the palms of his hands. “It’s for the best,” he reassured her, brushing her nose with his. “I’d love to live with you, it’s just not the right time yet, is all, okay?”

“Okay.”

Jess kissed her softly to seal the promise.

 

**AGE TWENTY-ONE. APRIL. PHILADELPHIA**

Truncheon was nothing short of amazing.

Rory wasn’t sure if she’d ever felt this proud of Jess in her entire life. The bursting feeling of happiness in her chest most certainly beat out the old burst that she’d felt for him on his graduation day. Everything that he’d achieved here was something that Rory _knew_ he’d always been capable of doing, and the way his face lit up when he saw her come through the door made her knees go weak.

The open house went smoothly, all arguments about what to name the bar they wanted to buy aside. Even Luke, estranged his daughter, April, and her mother had shown up to support the entire thing. Rory had been shocked to see her own mother there, but Jess had pulled her to the side and said he’d invited her since _Uncle Luke_ was being kind of an idiot with this whole April thing. Rory watched the way her mother happily engaged with Luke’s daughter and the way it seemed to alleviate the stress off of Luke’s face, and she’d never wanted to kiss Jess harder. He’d practically fixed Luke and Lorelai’s biggest issue almost single handedly.

Jess took her all throughout the storefront, introducing her to his friends (Jess had friends!), co-workers, and clients. Many people asked if they were together, and Rory blushed as Jess calmly explained that she was his best friend and nothing more. It was almost disappointing, but Rory couldn’t get upset with the obvious truth.

He’d introduced her to a skinny, petite girl named Valerie Marquez, and Rory immediately recognized her voice. She’d been the woman who’d answered Jess’ phone. Rory watched them interact with quiet interest, her eyes darting back and forth as she took in both of their faces. There was a lightness to Jess when he talked with Valerie. He smiled and laughed more, and Valerie touched him _a lot_ and giggled _a lot_. Rory quietly resigned herself to the idea of them dating.

When the whole thing was over, Rory found herself sitting in the now cleared out poetry reading area, thumbing quietly through Jess’ book. She’d read it so many times, that she probably could’ve gotten up on that makeshift stage and recited the first three chapters off by heart.

Jess came over and sat with her, teased her about reading his book for what seemed to be the millionth time. They bantered and talked about her job as the editor for the Yale Daily News before he convinced her to come out to the bar with him and his friends. And that’s how she was sitting in a booth between Jess and his friend, Chris, sipping quietly on a vodka cranberry while the group talked amongst themselves. Jess’ friends were insanely nice people, Rory decided. They treated him like family and had been really welcoming to her, even Val, so Rory couldn’t find a thing to complain about. Plus, she was three drinks in and feeling kind of good, not crazy drunk, but still good.

“You want another?” Matt asked her with a smile she found kind of charming.

Jess laughed. “I don’t think you’re ready for stage four Rory Gilmore.”

“What?” Chris asked, looking intrigued and Rory felt her face burn.

“Shut up,” she said to Jess, but he ignored her.

“Rory has drink levels. Up to three drinks she’s fine, she might stumble a little bit she’s pretty much the same as sober-Rory. But four-drink-Rory is where it gets interesting. She gets reaaaal _confident_. Then five-drink-Rory gets flirty, six-drink-Rory is just horny, seven-drink-Rory is sad and crying about everything.”

“My cut off is four tonight,” Rory confirmed, blushing at Jess’ explanation of her drinking habits. “Confident Rory can hurt no one.”

It seemed like a good idea at the time and Rory had an incredible night out. It was definitely the most fun she’d had since her fight with Logan, and she hadn’t really thought about him at all tonight. That was, until he called her to tell her he made it safely to the destination of his big stunt. It’d really soured her mood, but four-drink-Rory still lived on—just a little quieter now. Jess was quick to notice the difference, but he didn’t ask her about it until they were back in the apartment above Truncheon. It was too late, and she was too drunk, to drive home now but she was pragmatic and kept a pair of extra clothes in her car at all times.

Jess led her to his bed and sat her down. “You good?”

“Just dandy,” she mumbled, laying back on the mattress and curling up into a ball. “Stupid Logan and his stupid stunts and ruining my stupid night and his stupid face.”

“Uh, I don’t think you’re good.”

“I’m fine!” She snapped, sitting up to glare at him.

Jess raised his hands in defeat. “Okay, don’t shoot.”

“May I please borrow something to sleep in?”

Jess recovered quickly, letting his arms drop back to his side. “Yeah, sure.” He made his way over to his dresser and pulled out a black shirt and some flannel bottoms and threw it to her.

She held up the shirt to read the writing and wrinkled up her nose at the band name. “Coldplay?”

“I like Coldplay.”

“They don’t seem like your type.”

Jess shrugged. “They’re an alternative band.”

“In _what_ world is Coldplay an alternative band?” She demanded, eyes narrowed in suspicion.

“Go get ready for bed.”

Rory sighed and scooped up the clothes he gave her before making her way to the bathroom, still stumbling and swaying a bit. Jess’ clothes were comfortable; they smelt like him and were of that well-worn, faded quality. She came back into the room to find him already in bed and she didn’t think twice before burrowing into bed beside him.

He viewed her out of the corner of his eye and didn’t flinch when she laid her head on his shoulder.

“You ready for bed now?” He asked and she nodded slowly. “Okay,” he said, shifting to turn out the lights.

Rory didn’t know how long they laid there in the dark, but she knew that neither one of them were asleep. Her mind was running rampant with everything that’d happened so far this year and last. Jess and Logan fighting, Logan breaking up with her via Honor, her horrible hookup with Dean, Logan and the bridesmaids, Jess’ letter, and now she was here laying in Jess’ bed

“Jess?”

He grunted beside her.

“Am I a bad person?”

“What? Of course you’re not a bad person.”

She sighed. “I think I might be.”

“Where is this coming from?”

Rory bit her lip, wondering if it was best to come clean or keep it vague, but four-drink-Rory didn’t lie—even if she was sobering up. “I cheated on Logan.”

“…When?”

“Earlier in the year,” she admitted.

“With who?”

“Dean.”

“Forester?” She could hear the judgment in his voice. “…Isn’t he married?”

“Yes,” Rory squeaked, shamefully. “I regretted it immediately, but I was sad and lonely and I know that’s not an excuse but… He was saying all these nice things and asked to talk to be alone and I should’ve _known_. I mean, I probably _did_ know, but I just didn’t care because I’m a horrible, selfish, awful person.”

“You’re not.”

“I am!” She argued. “I really, really am.”

“Rory,” Jess twisted onto his side to face her in the dark but she stayed on her back. “You made a mistake. Everyone fucks up sometimes, it’s not the end of the world. You did what you could to fix it I presume since you’ve been back with Logan for months.”

“I told him immediately but then…”

“But what?”

“Then I found out he cheated on me in December with _three_ girls! Not just one! _Three!_ And I would’ve forgiven him if he’d just told me when I came clean about Dean, but he just kept it to himself until his sister’s wedding and I found out from the girls—not him. And I let him talk me into forgiving him and I’m so stupid, because he’s right, I have _not_ forgiven him! I don’t know if I _can_ forgive him!”

Jess sighed and was a torturous sound. “I thought you said everything was fixed.”

“I… Well. Everything but him, I guess.”

Jess didn’t say anything.

“I’m sorry,” she said meekly.

“For what? I wasn’t wronged here.”

“I know but… you probably have a very clear expectation of me and I’m not living up to it.”

“Rory, that’s not true. I don’t have any expectations for you. You don’t have to impress me or live up to some weird standard. I’m _me_ , and it would be ridiculously hypocritical to hold you to a standard that I can barely even reach. If you’re disappointed in your actions, that’s simply you being self-reflective. I have nothing to do with it.”

“I just…” She paused as sober-Rory tried to fight against four-drink-Rory and lost. “I don’t think I’m good enough for you.”

“What?” Jess asked, sounding incredulous. “Rory, we’re _best friends_. Have been since we were sixteen. We’ve both made mistakes and we’re still here.”

She twisted onto her side almost came nose-to-nose with him. Just a few more centimetres closer and she could kiss him, though sober-Rory screamed at her not to. Rory bit her lip, leaning in a little just as Jess turned back toward the ceiling. The rejection spread throughout her chest like a burn from the inside out. What was she doing? Who was she becoming?

“You don’t want to make any more mistakes,” Jess said calmly, and it brought tears to Rory’s eyes.

She nodded. “You’re right.”

“We’ll talk about this in the morning when the alcohol isn’t messing with our heads.”

“Okay,” she whispered, but she barely slept at all and when she did she dreamt of herself straddling Jess’ hips and placing searing kisses on his neck.

She awoke to a hot pulse between her thighs and there was a sticky wetness that made her underwear cling to her more than she’d liked. Maybe Logan was right, maybe she did need to back away from Jess Mariano.

 

**AGE TWENTY-THREE. SEPTEMBER. BOSTON**

The past few weeks at work had been horrible.

Unfortunately for her, the Huntzberger take over was very much so a reality, though the CEO of Metro _was_ trying to fight it. Rory had spent hardly any time working on her assignments, instead she spent most of her time working on finding a new job. There was no way she was going to let herself live under the thumb of the Huntzbergers again. She’d gotten out from that life and she had no intention on going back.

Of course, this news came just a couple of days after she signed the lease to her new apartment, and now there was a real possibility that she wouldn’t even be able to afford living there. Rory didn’t know how it was that Logan Huntzberger managed to literally fuck up _everything_ in her life, but she supposed it was just one of his many talents.

This stress hadn’t been necessarily good for her relationship, either.

She and Jess had been at each others throats lately over the most dumb of issues. She knew he was right about why they couldn’t move into together, in fact his reasons for _why not_ had been her reasons in the first place. In the end, she just liked what a great supportive rock he was to her, and she was afraid that if she moved out she would lose that.

The more rational part of her brain told her that Jess would always be there, just like he always had been, but the clingy girlfriend part of her was having a really hard time letting go. By the time Saturday rolled around, it was almost as if the universe agreed that Rory was getting too clingy and it was high time to force her and Jess apart. It came in the form of a phone call by her very own father who wanted her to try and make a trip down to Boston to come see him and Gigi.

Normally she would’ve said no, but Jess looked eerily exhausted from dealing with her and Matt and Chris were avoiding her, so she took a deep breath and gave in. Besides, she hadn’t seen her dad and little sister in almost a year, and that was unacceptable. One of her New Years resolutions was to see them more, anyway. To deny the opportunity would be to go back on her word, so she packed an overnight bag and went to see them the very next weekend.

And now she was in Boston, laying on her father’s couch and questioning her life choices. Gigi was happily watching her favourite cartoon beside her and drinking a juice box. Just seeing her little sister so content and happy made Rory desperate to rewind the clock and somehow become a child again.

Her phone light up on the coffee table, shrilling in a peppy ringtone that she’d only saved to one person. Rory felt her heart jolt a little bit when she answered, her voice cracking as she said, “Hello?”

_“Rory, hi! It’s Avery Ramesh.”_

Rory smiled to herself. “I know, I have your number saved.”

_“Oh! That’s unexpected, but nice.”_

“What’s up?” Rory asked, pushing herself up from the couch and into the kitchen once Gigi gave her a dirty look for talking while her show was on.

_“Nothing much, really. Jess told me you were in Boston, so I thought maybe you’d want to get lunch or something?”_

“I’m actually babysitting my little sister while my dad’s at work… I mean, I could bring her but she’s kind of _really_ into _Shaun the Sheep_ right now..”

_“That’s okay! I could come to you…? Or is that overstepping?”_

“No, no! That’s perfect, I’d love to have some adult interaction,” Rory said, looking across the room at Gigi who’d started giggling uncontrollably at the television.

_“Okay, I’ll bring food and wine! Text me your father’s address?”_

“Perfect! I’ll text you the address ASAP, okay? See you soon.”

When Avery said goodbye, Rory immediately texted her Chris and Gigi’s address before heading back to the couch and settling in next to her little sister. She didn’t know how many more episodes of Shaun the Sheep would be playing, but somehow she didn’t mind it at all. Rory stifled a yawn behind her hand and let her eyes close for a quick nap which seemed to last a little longer than she intended. By the time she woke up, the house phone was ringing and Gigi had switched over to watching Spongebob Square Pants.

Rory stretched her arms above her head before grabbing the cordless off the base and answered with a tired greeting.

 _“Hey,”_ Avery said, and Rory shook off the sleepiness, _“I’m downstairs! Can you let me up?”_

“Of course! Hold on, I can’t remember the code… My dad wrote it down for me somewhere…”

“It’s 88!” Gigi called to her, her skinny little arms hanging over the back of the couch as she stared at her with big curious eyes.

Rory pressed the digits on the phone, bid Avery goodbye and started pacing as she waited.

“Who was that?”

“A friend.”

“Your boyfriend?”

Rory shook her head. “No.”

“Girlfriend?”

She furrowed her eyebrows together and stopped pacing, pivoting on the spot to look at her five-year-old sister. “What?”

Gigi shrugged. “Mommy has lots of girlfriends. You know… friends who are girls.”

“Oh,” Rory breathed a sigh of relief. “Right. Of course. Then, yes, she is a friend who is a girl.”

Gigi nodded, seemingly satisfied by that answer and she happily went back to Spongebob.

The knock came at the door just slightly after and Rory invited a wind swept Avery into her home. Her friend’s curls big, voluminous curls were all over the place, some were stuck to her glossy lips. She had two bags of food in her hands and a bottle of wine tucked under her arm.

“Hi,” she said breathlessly, and Rory took the bottle from her when it started to slip.

“Hi.” Rory smiled, watching her toe off her heeled booties and put the bags of food down to take off her coat. Rory rushed forward to grab it and hang it up in the closet before gesturing Avery into the main area of the apartment.

“Wow, nice place. Your dad has good taste.”

Rory laughed. “He’ll be happy to hear you say that.”

“Do I get to meet him?”

“Maybe. He should be home at around three, but I don’t know how long you’re staying?”

“However long you’ll have me,” Avery said.

When they got the kitchen, Gigi was ransacking the cupboards looking for a snack. Rory pulled her away as she almost caused all the contents to tumble out by moving a soup can.

“What are you looking for? I’ll get it for you.”

“I want gummy bears,” Gigi said, looking up at Rory with her big, pleading eyes. Rory looked at the time on the clock, it was just a little past twelve so maybe gummy bears wouldn’t be so terrible.

“Okay, fine. But, be polite and say hello to our guest first. Her name is Avery.”

Gigi peered past Rory’s legs to get a better look at the other woman in the room. “Hi,” she mumbled before running back into the living room to continue her television binge.

Rory sighed and fished the gummy bears out from the pantry before giving Avery an apologetic smile. “She’s kind of a brat.”

“I don’t mind. Here, I’ll give her the gummy bears.”

“Are you sure?” Rory asked, nose crinkled up. “She might bite you.”

“Does she have rabies?” Rory shook her head with a quiet laugh, and Avery grinned at her. “Then I’ll take my chances,” she said, holding out her hands for the candy. Rory handed the pack over and watched as Avery made her way into the living room.

Rory found herself creeping a little closer to hear their conversation and felt a little light when she heard Gigi giggling and Avery making funny noises. She bit her lip in embarrassment once Avery caught her eavesdropping, but her friend didn’t seem to mind.

“I’ll be back to watch Spongebob with you after,” Avery promised Gigi before getting up and coming back into the kitchen. She placed the bags she’d brought in on to the kitchen counter and pulled out bags of chips, popcorn, and some cartons of dim sum. “You like dim sum, right?”

Rory nodded. “Love dim sum.”

“Great! Does Gigi like it?”

“I… actually don’t know.”

“Well, I guess we’ll find out. If not, I brought lots of chips and if that fails… more gummy bears?”

 

**AGE TWENTY-ONE. APRIL. PHILADELPHIA**

The next morning wasn’t as awkward as Jess thought it would’ve been. Rory acted like nothing between them had happened (not that anything really _did_ happen), and Jess was more than happy to follow her lead.

Matt, Chris and Austin were all up and sitting around the living room with breakfast and Jess poured Rory some coffee as she got ready for the day in the bathroom. When she emerged she was in the fresh pair of clothes she’d taken out from the car last night. She looked tired, there was definite bags around her eyes but she wasn’t acknowledging it, so Jess kept himself silent.

The boys talked to Rory more than he did, and he went about his usual routine as if she weren’t there—mainly because it was easier.

His head was still reeling a bit from her confessions last night, and the way that she’d kind of tried to kiss him. It’d be dark and he couldn’t tell exactly what she was doing or how she was feeling, but the room had quickly filled with tension and Jess had turned himself away from her at just the right time, he thought. Her reaction only seemed to further the idea that she was trying to do what he thought she was trying to do.

In the end, he was just happy that they weren’t talking about it.

He took a long, hot shower and allowed himself to really just get rid of whatever stress had knotted itself up in his back and shoulders. When he got out of the shower, Rory was pacing around the apartment frantically, cellphone to her ear. The other boys were looking at him in relief, as if they hadn’t known what to do, but Jess just stared back in confusion.

It was Chris who got up to talk to him quietly. “Rory got a call from Logan’s sister last night, but her phone was dead until she charged it while you were in the shower… She left a voicemail. Logan’s in the hospital.”

His tongue felt numb and heavy in his mouth. “He’s what?”

“I don’t know the details.”

Jess ran his tongue over his teeth and thanked Chris with a nod before moving off to Rory, who was clearly trying her hardest not to become a crying blubbering mess. Her phone call was done and he’d only caught the tail end of her thanking Colin for all his help. He steeled her, hands on her shoulders and coached her to take in deep breaths. She started to cry the moment she laid her head against his chest and he wrapped his arms tightly around her.

“Shhh. It’s going to be okay,” he tried to comfort her, but really he didn’t know any of the details to feel comfortable saying that at all.

“H-he got lucky,” Rory choked out, pulling back to look at him with red-rimmed eyes. “The doctor said he could’ve been paralyzed, but he should be able to make a full recovery.”

“That’s good,” Jess said softly, tucking a stray strand of hair behind her ear.

“His dad didn’t even show up and his mom locked herself into a spa! Honor would go but she’s on her honey moon or something, I don’t know. He only has Colin and Finn, and I should… I should be there.”

Jess hummed in agreement. “Yeah, of course.”

“God, while he was… while he was _hurt_ I was here doing god knows what!”

“You can’t blame yourself, Rory. You didn’t know this was going to happen.”

“Yes I did!” Rory argued. “I did! I did know. He said he was going to do this stupid stunt and I said it was dangerous and he accused me of just saying it because I was mad at him and _not_ because I was worried. He wouldn’t listen to a word I said, and I didn’t even _try_ to fight him on this ridiculous idea! What kind of girlfriend just goes off and lets her boyfriend almost die while she parties it up with her best friend and thinks of… of…” She trailed off and Jess didn’t need her to continue.

“Rory, he’s a big boy,” Jess said, voice hard. “He was going to do whatever it was he wanted to do, no matter if you agreed or not.”

She was silent for a beat before she nodded, wiping at her eyes with the heels of her hands. “I should… I should go,” she said firmly and Jess took a deep breath. “I’ll call you when I’m settled?”

“Sure. Take your time.”

She stared at him oddly, almost as if this were the last time she was ever going to see him. He gulped against the lump that randomly formed in his throat, and he held his breath when she leaned up and pecked him very, very softly on the lips. It lasted for less than a second and it was so soft he didn’t think it’d actually happened at all.

“Goodbye, Jess.”

He licked his lips, still feeling the tingle from the phantom kiss. “Bye, Rory.”

 

**AGE TWENTY-THREE. SEPTEMBER. BOSTON/PHILADELPHIA**

“So, remember the whole Huntzberger thing?” Rory asked Avery once Gigi was asleep on the couch and the television was on mute.

Avery had her curly hair gathered up in a loose, fluffy bun on the top of her head now and Rory took in just how petite she really was. Her whole body was dainty, but her wild mane kind of hid it all from view.

“I do.”

“Turned out to be true,” Rory said with a sigh. “My boss is fighting it, but it might actually come to fruition, which isn’t good. I don’t want to be there while it happens, so I’m looking for another job entirely.”

“Sorry,” Avery said softly, playing with the rest of her dumpling that she’d yet to eat.

Rory peered at her curiously. “Why?”

“I didn’t want to be right.”

“Oh,” Rory nodded. “Yeah, I didn’t want you to be right, either, but it’s okay. I’m saying positive and I know I’ll find something sooner or later.”

Avery got oddly quiet before she said, “I wish I could help.”

“You have,” Rory promised. “You warned me, so I wasn’t shocked and looking for jobs hasn’t been easy but I’ve been prepared, too.”

“Are you sure?”

“Completely.”

They changed the topic then, talking about everything and anything except the Huntzberger takeover. It felt like they’d been friends forever, despite that hardly being the case. It felt nice to have another female friend who wasn’t Lane Kim or Paris Gellar. She’d loved being close with Olivia and Lucy back at Yale, but they’d fallen out of contact since graduating and both of them had moved away kind of far, so seeing each other was almost completely impossible.

But, Avery Ramesh was genuinely nice, and sweet. There was no cattiness or bitterness, and she went out of her way not to bring up her old relationship with Jess, which Rory appreciated and showed her respect for by also not talking about her own relationship with the boy they had in common.

Even her dad had wound up liking her, though Rory couldn’t be sure who wouldn’t.

“You mean even Gigi was receptive? Wow, that girl is _magic_.”

“I think,” Rory started, having thought on it a little more since Avery’s departure, “she’s just really maternal and supportive, so she makes everyone feel at ease.”

“That’s a great personality to have,” Dad said and she couldn’t help but agree.

In the past, Rory had wondered just what it was that Jess saw in Avery, but now she knew. Rory had never considered herself a religious person but she was more than certain that Avery Ramesh was a literal guardian angel.

Her final night in Boston flew by quickly. Gigi kept her plenty busy, and when Gigi wasn’t demanding all of her attention then her man-child of a father was, but in the end this weekend had turned out to be exactly what Rory had needed. She’d gotten away from Jess, loosened her tight hold on him a bit, and actually found herself a little excited about moving into her new apartment in the next couple weeks.

Philly was the exact same as she’d left it, and when she got into the apartment, Chris, Matt, and Jess were all sitting on the couch with a couple of beers and playing video games on the television. They all smiled at her in greeting, but only Jess got up to welcome her home properly. He kissed her, long and hard in a way that she’d missed but hadn’t exactly been dying for in her time away (which she thought was a good thing) and then kissed her cheek.

“How was your trip?” He asked, gently taking her bag from her.

“It was amazing, actually. Much needed TLC. I’m sorry for being such a clingy monster recently.”

He shrugged. “It’s okay. Sorry for being a little cold and distant.”

“You weren’t that bad, honestly.”

“Huh. Shocking.”

She smiled at him and kissed him again. “I hung out with Avery. That was fun, actually! She’s probably the sweetest person I’ve ever met and that’s saying something because I’ve known Lane Kim since I was _four_.”

Jess laughed as he took her bags into their bedroom and she followed. “She is pretty nice.”

“Do you think she’s human?”

“She’s definitely human.”

Rory sat down on the bed. “She just seems so… perfect,” she said and it must’ve sounded kind of dreamy because Jess threw her one of those teasing looks he only reserved for the _Avery crush_ as he called it.

“Trust me, she’s not perfect. She’s very calm and patient, but when she gets mad? Run. Plus, she can be a little demanding in what she needs from a person. I adapted well to it, surprisingly, but,” he shrugged. “Not to mention, she’s very head-strong, which can be a negative thing sometimes. We all have faults, I wouldn’t put her on a pedestal.”

Rory hummed. “I suppose that’s fair. I actually couldn’t help thinking of her as a guardian angel.”

Jess laughed from his belly and it was prolonged and left him a little breathless.

“What?” She asked indignantly. “If she hadn’t come back into your life none of this would’ve ever happened. I mean, she would’ve never invited us to the Gala, you probably would’ve never asked me out, and she would’ve never let Logan and told me about the takeover… I mean, come _on_ , you have to admit that’s kind of freaky that her entire existence set everything in motion.”

“I’m laughing because I thought the same thing a few months ago.”

“Really?”

“Mhm,” Jess nodded.

“Wow.” Rory crossed her legs on the bed. “Our very own guardian angel?”

Jess sat down beside her and ran his fingers idly through her hair. “Yeah, maybe.”

She looked into his eyes and basked in the love that she saw there. Rory leaned forward to capture his lips in a nice, slow kiss before Jess quickly took control and it turned hot and dirty really fast. He nipped at her bottom lip and she gasped, opening her mouth up to him and shivering at the feel of his tongue against hers. He laid her down on the bed and she uncrossed her legs and spread them so he could fit between her, grinding his pelvis against hers and causing beautiful, but torturous friction between all their layers of clothes.

“Wait,” she said softly and he leaned back to look at her. “Sex playlist.”

His brown eyes were hazy with lust, but he managed to process what she was saying as he nodded and clumsily climbed off of her to grab his laptop and soon enough the music started to play at full volume and Jess firmly shut their door.

There would be no more running away from Jess Mariano from here on out.


End file.
